I currently wake up way too early to work as an aircraft mechanic and I am itching to progress into some buy and hold property investment.

I suggest you study "Encumbrances to Real Estate" and "Liens" from taxes, mechanic's liens, mortgage liens and judicial or judgment liens.

Probably very cool... that is of course if you enjoy rehabbing... or having lethal synergies behind rehabbing that pretty much can help you outgun your competition not only from the creative strategies of saving the deal using the straddle play, but extrapolating this deal further into greater profits, with use of creative rehabber synergies and creative money saving mechanisms in context of adding upside value to the property while simultaneously making sure that folks who live in your property end up not creating havoc and end up paying you rent in a motivated manner.Combine all that with commercial multi family real estate inter mixed with raising money for for private lenders and multiply that by the number of multi units in one complex and creative tax strategies and you get yourself a wild wild synergy, helping you save the deal and go beyond.Sorry if I am too theoretical... but it is what it is.

I've searched a bit and have not come across a post that quite fits an investment opportunity I have been looking into.At the bottom I put a cliffs notes version of the building/surrounding area (probably could have shortened it up, and maybe I'm looking at too many external factors - however let me know)My thoughts - building would be good structurally/mechanically - located in the downtown core - building is already built out into 4 offices and reception area main floor with a kitchenette/half bath2nd floor has 7 offices, 2 baths, 2 storage rooms2 entrances into the building, street parking on 2 sides, building is located across from the local courthouse(Could potentially turn the upper floor into a couple of apartments or one large apartment - rent for 800-1k a mo for one large apt, however rehab $$ would climb - city would be more than willing to change zoning for this and encourages this type of arrangement in the historic buildings - ie office bottom floor, apt top floor)$60k Purchase Price$20k Rehab budgetPotential gross income $2800 per mo (7 offices $400 ea)Guesstimated Pro Forma--  $33600        Gross Income - 7 offices $400 ea       (5040)        15% Vacancy       (2400)        Property Tax       (2500)        Insurance       (6000)        Utilities - figured $500 per mo/gas/elec/water- think this is high though       (1680)        Cap Ex       (4980)        P&I Pmts $60k loan 5.5% interest - 20 year amortization       (4800)        Janitorial - $400/mo - this would probably be lower----------------------------------------------------------------------------------$      6200        Cash FlowI think I could improve on the above cash flow, not sure the Insurance is 100% accurate, could possibly increase gross income if I have more than 7 offices etc.  

You do not need to be a mechanic to own a car.

If all the mechanical systems are good and the units are in decent shape, you can spend most of it on updating your unit to a higher quality apartment that will pull more rent when you vacate. 

What they do not do is fix all the roofs, mechanicals, etc. that will eat up the new buyers in the first 5 years or so of ownership.

So, work on a good script, practice it and role play, then make the script your own, or make it fit your personality so it doesn't make you sound mechanical. 

The house overall is in great structural and mechanical condition, just needs whole house updating.

In my prior post I describe the mechanics of properly assuming a loan... if you would like either coaching, evaluating the deal with a second set of eyes, or help acquiring and negotiating the  delinquent fees then please feel free to reach out to me as I am an investor in Chicago.