There are probably going to be a lot of options available depending on how your portfolio is structured. 

I understand that they are looking at income and assets… my question was specifically about how mortgage companies view depreciation on existing properties… It depends on the loan product, do you know what the specific loan type / mortgage lender you are working with?

There is a lot to it, so it's going to be an 'it depends' kind of answer.

Depending on the structure of the LLC (e.g.

I agree the cut from a typical short-term rental manager is a good chunk and I doubt we will cash flow much if at all with a PM depending on their % take.

Bart, it just depends on what your investing strategy and your priorities are.

The tricky part is separating out the smooth talking contractors (that suck) and the capable, dependable contractors. 

If so, then what I would do is- 1) You mentioned 'wooded' lot, so depending on how much wood we are referring to, I would seek and get bids for selling the wood (I dont imgaine it would be much if anything at all cosidering .34 acres) additionally, you don't want to get rid of every tree; 2) When you split, you can certainly put restrictions in the new deed, i.e. any future structure being build most be between 1,000-1,500 sq.ft., must be single-family use... etc., etc. 

More DSCR lenders do suburban STRs, but some can do rural as well, the best lender for you would really depend on the property details and your long term investing strategy.

The HELOC has a start rate of Prime 8.5+ 3 ish, depends what your FICO is.