I am planning to just have a very basic plan just incase we got hit by a bus...And a big fat bank account will help with your confidence.

I'm thinking I can later cash-out refinance into a loan (possibly a VA loan) to finance another deal and wrap the new mortgage so as to keep the installment payments in place and avoid hitting my retiring family member with a big fat tax bill. 

There's a belly in the cast iron sewage line that's about 10' long and about 40' from the house causing the sewage to settle and "back fall" a bit. 

@Billy Bell  I think the first thing you have to realize is that your not the only one doing this.. its huge business to sell yellow letters... 95% of the people that do this do it for 6 months never get a deal and quit...I would suspect your absentee owners in your areas get a lot of letters.. so its a numbers game and you have to stay at it for years..

REMEMBER: Pigs get fat, hogs get slaughtered. 

Chicago code is that EACH habitable room must be at a SUSTAINED temerature of 68 degrees F during the day and SUSTAINED 66 degrees F at night.

Even if you are holding the cash on the sidelines while you look for a deal, you still are better having access to the cash instead of having a fat balance sheet.

Start with: title company plat map, go belly up to planning desk and talk about your idea.

Furthermore, you need to understand the risk associated with real estate—things are great right now, but can you sustain if your investment market goes belly up?

If by special you mean you no longer want to rely on someone to pay you what THEY think you are worth or you have so much fire in your belly that you just want to do deals all the time even while you are working on your regular "job than yes, IMHO it does take someone special.