I'd sit down with a real estate savvy CPA and go over the numbers.

Since then I’ve bought 14 houses from equity just sitting in properties doing absolutely nothing for me.

I've noticed in my area that houses that have been converted into 2 units tend to sit on the market for much longer and sell for much less than traditional single family houses with similar sqft and finishes.

HELOC bank doesn't want their line used as a term loan on real estate they don't have collateralized and the bank that you apply for a loan for doesn't want your down payment to be borrowed.If you wanted to get the HELOC for home improvements then decide to draw on it for liquidity, had it sit in a bank account for a couple months and then applied for a MF loan and used it as the down payment, you'd have to answer no to the question, "is any part of the down payment borrowed".

I'm just thinking it's better for the bank because I might have to move out due to financial reasons, and then the property will be sitting here vacant, leaking and with a developing mold problem that will go from just one wall to the entire house if not taken care of.

The rest is sitting in the savings and waiting to be used on the next deal if/when it presents itself.

All this summer every booking has been last minute, within a week or so of the stay, so it's obvious to me people are still just sitting on the sidelines looking for the best deals since there's so much supply out there.I think it will start thinning out over the next few years - I've seen a few places in my own community that I know were STRs that have been sold as owner-occupied (hard to make a 4/3 STR work down here when you're paying $450k or more), so as that starts to happen more and the building pushes even further out into the hinterlands I have hope for the future.

I have a pretty large balance sitting in an account with her which included balances From not getting paid the last two months of rental income and  tenant deposits and maintenance reserve funds. 

I am actually sitting in the airport going to close on 2 doors in an area where they are. 

If it sits empty for two months, they still get paid.