A small repair job could turn into a very expensive job because of their failure to notify you of any problems.

And now, back to your regularly scheduled programming ;)

The subfloor main level was unusable and It was sight unseen....total gut job $100k rehab.

If you can not schedule it on your lunch hr. you take a vacation day or call in sick.

While that's possible in a series LLC, you start making the accountant's job quite difficult and it may make sense to have separate traditional LLCs.

At first I'll be doing it part time as I have a full time job. 

Once it's been condemned and demolition scheduled it is extremely difficult to reverse the process. 

Working a 9-5 job with very little return in a 401k and Roth IRA and having to work until I'm dead is not a life I want to lead.

Your job is to determine if the risk is worth it.If you are are just thinking out loud that you may want to sell in 5 years, given your own statements that it is making great cashflow for 5 years, then who cares? 

@Eric SmithI would use 99Designs for higher budget jobs and Fiverr for lower budget items.