If I can catch-up and finish a couple projects this winter I am hoping to have solid plans next summer. 

As far as DIY, painting will be tedious and time consuming, but if you break up the trim and the rolling between two people, it could take you a couple of days to paint a whole place, and it will save you a ton of money.

I was hoping to work another couple years, but actually I find it so much easier to manage my properties or go find new deals without a job. 

I am in negotiation for a couple of properties up there and want to interview property managers. 

Besides getting a couple more quotes, the question is who is liable.I plan on repairing, paying the @$10k, and work with them after the fact.  

If you are looking for meetups to attend, I attend a good one tomorrow night at Dino's pizza in Chicago.

You're by the water, so a couple of specimen-sized palms somewhere would definitely be in order.All this should be easily done within your budget, and will DRAMATICALLY change the outward appearance/curb appeal and VALUE of the property, no question.Esthetics for a property don't have an exact mathmatical equation for ROI.

When i call back later, when im available, i always apologize and say i was doing a walk through or looking at another property lol @Nzinga Augustoi personally wouldnt do #1 or #2 for a couple reasons, Lets say you get a call at 830 Am and the VA sends you the info......you cant call until after 5 anyway.......same thing your voicemail would do...........also, i would keep your costs low until youre getting consistent deals.......just my opinion. 

I certainly didn't volunteer the information.A couple months ago I put a Heloc on my house just in case  I don't remember them asking if I lived there but they probably did in the ppwk somewhere.

I am not overly-handy (I never owned tools until I bought a duplex) - so far I've done basic electric (installing an outlet, adding a junction box, putting in receptacles, removing breakers, fixing a 3 way switch -- all things an electrician wouldn't touch -- or would charge a couple hundred bucks to do, cost me about 7 dollars - literally), replaced an exterior door, removed rotten siding and put up new siding along with replacing the plywood behind it, re-built the rotten framing of a garage wall, installed a ceiling fan, and just about a thousand other things along the way.