Also find a good lender that is well versed in STR/MTR loans to make sure you qualify for financing (if you need it) and that they can execute the loan smoothly

I've had qualified renters move into a rental, add their bum friends or family members, and then disappear, leaving me with bad renters who weren't approved and aren't on the lease.The best practice is to screen every adult, approve them, and add them to the lease. 

The borrower will need to be exceptionally qualified and have significant reserves (particularly for a jumbo or super jumbo loans of $1-2-5M++) Historically borrowers could qualify with 10-20% reserves of the amount financed, that could jump to 100%+ without significant state and federal intervention.

So you feel like you get plenty of money from your not paid off rentals that allow you to quit your full  Having enough cash flow to quit your job isn't a requirement to qualify for cash flow.If you have to have a paid off property to get positive cf, does that mean I have to give back all my positive cf while I had mortgages on a property?

My thoughts would be to discuss it first with the township, then have a qualified investment savvy realtor tour the home, get you a CMA on the current property and ARV to compare.

Similarly, the sale ($575K) minus your adjusted basis determines your capital gain.You may qualify for the primary residence exclusion (up to $250K single/$500K married) if you lived there 2 of the last 5 years.

At the price point you qualify for, I'd be looking at a more landlord friendly state with more approachable price points.

If there is a large amount of equity, one party may have to buy out the other - if they cant afford it/cant qualify, then the property is sold.I deal with this frequently with mortgages. 

As long as the rents can cover both the current PITI and proposed P&I payment, credit is at least 680. you should be able to qualify. 

HELOCs are fine, but keep in mind that you really only want to use 50 percent of less (each) of your available equity just so you aren't creating a problem that you can't solve later if the value of your personal residences fluctuates.If you both have W2 jobs though, have you looked into getting qualified together and just getting a loan, 10 percent down each?