I found a licensed GC and started giving him small jobs, first the exterior paint, then the interior paint, then I just had him finish the job as he did good fast work for me.

You want to keep up the interior and exterior as pristine as you would expect a Hilton Hotel to be, while maintaining an aura of a friendly home.Being cheap is a sure way to failure. 

I run a small lodging property. 2 story exterior.

So I used the good will I had with some contractors to put a new roof on, new full exterior paint job, HVAC repair and some other odds and ends; and bill to escrow (so they'd get paid once we close), total about $5500 in work.

My skill level is limited to upgrading an existing space with new paint, fixtures, flooring, and lighting; this includes exterior painting, roof shingle upgrades, and deck building. 

A couple companies I’ve subcontracted with in the past and had positive experiences are Elite Exteriors. https://www.eliteexteriors.us/ Also ABC seamless siding. http://www.goabcseamless.com/Best of luck. 

Exterior Painter/Vinyl Siding3.

This will be for the exteriors. 

I also have family in the area who can check out the exteriors of the properties for me.I am looking for general tips of how to manage the process and things to look out for.

Originally posted by @Chris Connolly:I believe you are able to do the repairs yourself, if you're hiring someone, they might have to be certified (or that's only when you KNOW that there's lead paint, ie having it tested or it show up in the disclosure) "The law requires contractors to get certified in lead-safe work practices if their work disturbs more than 6 square feet of paint on the interior or a 20-square-foot section on the exterior of a home built before 1978."