It's a pain in the butt, and while it may be worth it to some folks, I don't see the value in it.Most of the stuff in that $1k-$5k price range has been picked over by local investors like roadkill picked over by vultures.

Anyways, as an Engineer I feel your pain in th dark side of construction as well ;). 

In the last 6 weeks alone, I’ve evicted a tenant (inherited) and cleaned out another apartment with so much trash and had a tree Dorian blew over on another rental.The lender stuff sounds like a major pain but that’s also seems par for the course.

It's had 20% equity for a while now, but the servicing company has been a huge pain to deal with and now that I kicked a couple of payments down the road when I asked for the 3 months due to Hurricane Harvey, they have stated I MUST escrow for the life of the loan.The mortgage is roughly $140K and it's appraised on the county tax rolls for around $215K, which is what I believe it would also appraise for with appreciation and some minor updates that I've done over the years, perhaps a bit more, $225k.Property #2 (now a STR – 2 units).

FWIW...In my experience, Albany County DSS has absolutely a pain to work with. 

Then at the next lease renewal we go up small amounts for the desirable tenants who don't create issues and higher amounts for the tenants who are more high maintenance and or pain in the asses. 

I have no doubt I could work twice as hard and find a better price on this or that but also know that the pains and potential problems that would come with vetting and working with a collection of new vendors that may or may not be reliable or do good work are not worth it to me. 

- Is it a painful process?

@Chris Hillthis decision is painful to say the least.

When it comes to painting exterior, you're looking for someone to pressure wash, prep the exterior (taping), caulk and seal where necessary in small cracks, around windows etc, prime and then pain with 2-3 coats.