I'm throwing mud at the wall, but it looks like you're cashflowing around $300 - $500 / month but not putting that back for your safety net.

Covered boat (and covered boat motor) with an intact not ripped, commercially available boat cover, on a trailer with inflated tires and a hitch lock.Set it on 3 pavers to help it not slip into the mud as much.

A house is a product, and like all products some are undesirable.

Also, from what I see, distressed properties are in an undesirable location for me as a single woman.

Look for things that will make it undesirable to future tenants like busy roads, no yard, no parking, quirky layouts, etc. 

I fixed an isolated rotted section of mud sill near the rear deck and I think it could hold an elephant now.  

If the property is in a MUD you’ll have that tax too. 

You could save about 40 percent of the full bid if you pieced it out.Hire a handyman to demo.Ask your handyman if he can do windows, doors, sheet rock, tape and mud, trim work,painting, tile work, hang cabinets, install vanities, etc.Ask him if he has tools, tile machine, compressor, hand guns,  Sometimes handyman are old General Contractors that didn't renew their paperwork.Hire a framer to remove or add walls and new rooms.Hire an electricianHire a plumberHire a sheet rocker and mudderHire window company or handyman to install the windowsHandy man can also do so much .Make sure the electrical and plumbing is done right.Most states allow $2000 of work for a handy man. 

I have spent many evenings watching them transform a property from undesirable to gorgeous.

Fixing the entire house the floors all had to be replaced and lots of drywall work, removed all the strips over the seems and mudded them out and sprayed knock-down thought out the house.