I wanted to wait out the winter to start on any repair projects but now while getting other quotes, I think the initial quote was very much under what I may be looking at to pay.

So let's look at the options.Option A: Pay Rent $3,000 a month.

It is likely that both you and your investment partner will need to pay taxes.

I found one self-paying tenant with a 530 credit score and eviction history.

But if you took a HELOC, which tends to have relatively high interest rates, your blended rate (the average of what you're paying on your mortgage plus the rate on the HELOC) would likely be in the same range as today's mortgage rate.You'd also only be renting out one unit, but by selling it might allow you to get more than one additional unit and still grow your portfolio. 

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

I rent nice places to renters all the time and they take good care of the property, pay rent on time, communicate well, etc.

If we kept it in our name for a year, does anyone know if we will have to pay transfer taxes when we transfer it to the LLC in both our names?

I could use the HELOC to finance my down payment and rehab and then when I refinance my BRRRR, I could pay off the HELOC and close the loan. 

So that by the end of the amortization schedule, almost the entirety of the monthly mortgage payment goes directly to pay principal.