Ideally I just want to start with one flip to gain experience and confidence.

So pick the better roofs of the four, get someone up there with a bucket of sealer, roofing caulk, if necessary a few bundles of shingles and patch it up until you have the funds to do a full tear off replacement.20 is a lot to manage part time, I have pushed it to 30 while I still had a corporate job with a lot of travel.

Taking off of work and having over a thousand in travel expenses without a guaranteed win did not seem worth it.I talked to the credit agency and it turns out this will ding my credit for the next 7 years even though the debt is fully paid off.

If you're not quite ready to self manage, I'd also meet with 1-2 other property managers just so you feel confident about whatever decision you make.

Zig Ziglar stated the salesperson's expectations have a direct bearing on the prospect's response so go in to each call with confidence (not cocky) and expect that the other person will want to talk to you. 

There's no shortage of people who have made it work with less going for them than you have so I'm confident you can find a way.

It should be... a place you lived in, or went to college in, or have family in, or can easily travel to, or want to own a vacation home in. 

I was also a travel nurse. 

Wholesaling can be a bit of a different beast compared to buy-and-hold strategies, but with your background, I'm confident you’ll pick it up quickly.I’d be more than happy to share some insights from my own experience in wholesaling or answer any questions you might have.

That’s one reason my realtor is pretty confident in the 1600-1700 range.