My biggest concern is finding the right contractors.

I wouldn't really look at these as an outright investment, but more of a retirement spot that you can try to generate some revenue from in the mean time.

At max 10k, I think my biggest issue is the maintenance upkeep

My hopes is that the "Biggest and the Baddest" Podcast continues!

My biggest advise is to not fall for lower price tag deals. 

Collecting rents is super easy and the bookkeeping features allow me to track all revenue & expenses for each property in a manner that makes filing my taxes at the end of year very easy. 

Anyone know of insurance that covers bed bug eradication and lost revenue? 

Albany was the biggest little town around for many years, but it has lost its way.

My biggest piece of advice would be to take it slow and learn to evaluate different options and strategies and hear different opinions (you don't have to take them all and use them, see what works for you... there are a lot of them on these forums LOL) as soon as you can.

Also, the biggest ticket item will most likely be the main sewer line disconnected, What was the quote for the repair?