By that time i expect the cash flow to play out like this:First floor unit: $1,400Second floor unit: $900 Three garage bays: $330Total expenses (PITI + 5% vacancy 5% repairs (1st and 2nd floors only)): $2,045Cash flow: $585 / month.

Any tips on evaluating an older property for repairs etc.? 

Yep.....no vacancy, capex, ongoing repairs, turn over repairs, management. 

He has a lot of experience with GCing and home repairs/remodels.

I Have a tenant that has a broken AC. I had a capacitor fixed a few weeks ago within hours of the notice, it was Saturday at 3. They called again tonight at 7 and said it was out again.

My guy said he could be out t...

Even if I could get a same caliber property for $140K it would still make no sense for you to assume all that risk (reno, repairs, etc.) just to have no upside. 

Purchase price 133,614Down payment (20%) $26,722.8After repair value 190,878 Property Taxes $255Home Insurance $66PM $160Mortgage $583HOA 0Vacancy (10%) $160 Repairs (5%)  $801600 Monthly rent-1304 the costMonthly Cash flow is 296Cap RateAnnual net(minus mortgage)/ purchase price10548/133,6147.9% cap rateCash on cashAnnual net/ Cash invested3552/26722.813.29% cash on cashNote: I haven't included CapEx.

You said the after repair value is $165k, how much are the repairs? 

All real estate is local so you need to attend local REIA meetings, any investor meetings you can find on MeetUp.com, local landlord association meetings.This is where you will learn who the players are in your area, how they find deals, how to estimate repairs, how to negotiate with sellers, which attorneys they use, which contractors, where they find deals.And finding buyers when you have a true deal is so easy.

If you have language in your lease that allows for entry to complete necessary repairs, I would give them official notice to enter and finish the window install by personally accompanying the contractor.