Just as the title says, i am facing a personal dilemma loaning a car to family.

I have loaned my 98 camry for more than three months to my family member who crashed into the back of a police officer on the highway on the way home from work. I am trying to get some opinions on reasonableness of the situation.

I insure the car and have kept it in top mechanical condition because i drive non stop for work all over the country.

For both my vehicles (98 camry/99 4runner) i pay $189 a month for high risk insurance. This particular camry has a value of 2500 but i only have liability insurance. I have been driving my 4runner. And had planned to sell the car in June, and offered it many times to this family member.

At this point i am asking my family to stop using the car, even though they offer to pay up on the insurance and have me keep it in my name so they dont have to transfer the title and register the vehicle. Either way this has caused quite a bit of friction.

I really wanted to invent the 2500 into the 4runner, and i am not a baller in a position to be giving handouts to family. So i expect them to pay the entire insurance premium for both cars, bc they are using my car and its like rent. Afterall, i cant go invest this money while they are racking up my insurance and driving around. Also need them to leave a check for 2500 so incase they crash and get hurt, i mean god forbid, i can recoup my investment.

Obviously not going to do this again, made a bad habit of having more than one car at all times when i owned a mazda and had to have two just to keep one running, lol

Anyone have policy or experience loaning cars to friends or family?

Yes, but it is about their history, not my kindness. If they were in an accident that really was an accident I can be tolerant and would not charge them anything.
If this was their third or fourth instance of immature behavior. They are on their own.

a) That's too long to "loan" anyone a car.
b) You're being taken advantage of.
c) Get out from under this asap. You may have some liability in case of trouble. I mean REAR-ENDED a police car? C'mon. I sure wouldn't want that person driving my car.
d) Just paying the ins. is no bueno ... see c) .... and you already have high risk ins???? Dude, end this.

You've offered to sell it to them and they refused to buy it.

Just sell it to someone else and the problem is solved.

Worried about the free loaders whining? Tell them you need the money for colorectal cancer treatment.

This. Get out. It'll probably cause bad feelings, but that's your bad for lending a vehicle without an endgame clearly understood by both parties.

Tell them you're putting the car up for sale, and they're welcome to have first crack at it, but one way or another it's getting sold.

Does this family member live with you, or an extended family member with a separate house? I understand you can't afford to give this person a car, but how "close" is this family member? I'd do more for an adult child/step-child than I would for a brother; I'd do more for a brother than an uncle, cousin, or nephew; etc.

Either way, you are being taken advantage of (see philsey's response above). Demand the past-due insurance payments at a minimum ($500-$600). You deserve more, but unless you agree to terms up front it's all but impossible to go after money afterwards. If you didn't set terms then legally you loaned him the car for free. If he refuses to pay even the insurance premiums then you're legally SOL. Consider it an expensive life-lesson.

Arguably this is where you would make a new agreement going forward. Say, $189 for insurance + $211 "rent-to-own payments". But in this case, in my opinion, you DO NOT want this guy driving your car around. If he gets in a wreck, then the other party can go after YOU if they want to. Plus is seems doubtful they'll bother to make the payments anyway. So feel free to try renting it with the title in your name, but personally I wouldn't risk it.

If the person lives elsewhere, then go get your car. This will generate bad blood, so park it in a secure location to keep him from simply taking it back. Also make sure he can't take your 4R in retaliation. Sell it, invest the money in your 4R.

If the person lives in your house, then this is more of a problem with regards to long term "bad blood", but easier to fix in the short term. Just sell it. Put an ad in the paper/craiglist/Facebook trade group, whatever. Show the ad to the family member to give them one more chance, but sell it either way.

What past-due premiums? You can't ask them to pay for insurance unless you talked about that before (and asking for insurance for both vehicles isn't reasonable). If you want to ask for compensation going forward that's different and reasonable, but the past is the past.

If you want to sell the car just sell the car

really? what state? the standard form covers household members and other permissible use

I've been in the same predicament as OP. It started with my loaning the brother in law a pristine, 180,000 mile '98 4Runner Limited 4x4 CA truck for a few months while he waited to deploy.

It ended up with my eating a $5000-6000 loss after he wrecked it while drunk one night in Jacksonville, NC and the family blaming ME for his DUI and basically ruining his career in the Marine Corps (I was 1000mi away when this happened). I had liability-only because he "promised" he'd get comprehensive on the car while he drove it. Went as far as to send me a picture of an insurance card. But I guess he didn't pay it.

Anyway, it can get really messy, OP, I suggest you cut bait now and get the car back.

I don't envy you, no matter what you do, you're the bad guy in this situation. No good deed goes unpunished.

When my son graduated he wanted to fly to his dad in Ukraine. I thought it was a good idea but i wanted to help him. I found tickets, hotel accommodation and I wanted him to be on the wheels. I found a place where he can rent a car in Kiev called Сar Rental in Kiev, Ukraine: No Deposit - Low cost - Rent Best Cheap Cars | NarsCars and you know I found a really great place. I made an order and when my son arrived in Kiev, the car was already waiting for him. He told me that European cars are really on a high level. Car was clean and in good condition so I was really glad that I found them.

Family and friends are the worst to be involved with on matters that can affect you monetarily and personally. What if they had killed that police officer? You would now be responsible financially or in some states criminally for his mistake. If they are your children that is totally different because in most states you are responsible for their behavior financially anyways..lol. But beyond that you have got to protect yourself just like the rich and powerful do. Get 2500.00 from him and give him a bill of sale for the car. This removes you from whatever liability he incurs in most states. Or sale the car to someone, anyone that way you are not the bad guy and you needed the money, period.

I'm confused

Did your relative crash the corolla or do they want to borrow the Corolla because they crashed their old car? I assume they crashed their old car.

If you give someone (anyone except for spouse) your car, the make sure that the car and insurance is in their name - even if you pay for it - then you are off the hook if they do something stupid again.

Me? Depending on who they are, I'd either give them the car or sell the car and tell them to go rent a car.