A lot of people recommend a separate LLC for each property and some suggest a trust or s corp that owns the different LLCs.

On large repairs like a roof replacement I would still want to get a bid of my own.It comes down to trust, if you don't have that trust with your PM then you might shop for another PM.

No matter how much money I may have I just can't justify buying a $90k car or a $1400 per month lease payment.

I’m thinking about selling one of my debt free rentals to pay off the loan of the new house – thus erasing the $3500/month loan payment.

If you're not a plumbing expert, hire a scope pro who understands plumbing and can walk you through everything (or have a trusted plumber watch the scope with you and explain it).I once bought a property where the seller had just installed a brand new sewer line.

Every lender will have their own method/calculation, but most lenders will assume some amount of a minimum payment and apply that in your DTI calculation. 

@Nathan Gesner I agree, because my rental is a business and I shouldn't waver away from the screening process even if its just a trusted contractor, but funding is what we need and I heard the SBA is a good source but is slow, thanks for responding.

So I have kept renting it out since then, taking a loss every year (rent did not cover expenses of taxes, insurance, maintenance, mortgage payments) so never any cash flow from it.

Even looking at the balanced rate (which I feel like is hard because the terms are different) along with the potential to have the monthly payment/fees covered, it feels like a cash out is a better option if we did want to keep this.Part of the current struggle is that the market was hit harder from the rate increase so sales are almost at a standstill and even with trying to sell the house, the rental market is doing substantially better because most military cannot afford to purchase in this area as the payments are over 6k/mo for buying vs 3-4k/mo for renting.Any advice is most appreciated!

Our payment is going up to $3700.