It’s expensive and painful.

I'd say that's worth it although the new ordinance saying it say to be linked is a pain. "$200 lease filing, $200 admin fee, $200 sanitation fee, etc." is likely what you'll end up seeing.

I know the pain.

The Delaware trust thing is scary to me because you're locked in- the more I read about it the riskier and more painful it sounds.

Getting a qualified, responsible, and smart tenant that is selfish lacks integrity can be a pain because they might even have the legal savvy to make your life not very fun.

This is for sure, my pain point. 

I really don't like snow and ice and traffic and it can be a pain there sometimes. 

(to get into the property it cost less than $5,000)Then the work started, LEARNING and GROWING PAINS (I knew zero about anything with this type of project) , rehabs, new leases, raising rents, etc. 

I've had 6 guests stay so far and have given 5* reviews, I'm still working on automation with cleaners and schedule's, but it's getting there.I decided to not completely refinance as I would rather have access to the LOC and didn't want to go through the nightmare of underwriting again as it is a pain for conventional financing with my long term rental portfolio and I have cheap (3%; 30 year locked) debt on this property already.Lessons learned?

I know it sounds like a pain - but it actually simplifies things in the long run - and we found that Lenders and local town PREFERS dealing with what looks like a LOCAL business.