The city will give you tickets that are not warranted.

Since conventional lending is not in my future for several months, I would be looking for subject-to, seller financing, and/or hard money, depending on the situation (still learning more about those).Naturally, going where the numbers make sense is my priority, but it would be a nice bonus if it were somewhere I myself would like to go or could realistically drive to in a day (or hop on a quick flight to).

For what reason are a lot of people going to spend money on a train ticket [which is expensive] to ride all day to get from Louisville KY to Indianapolis IN or Chicago IL???

A $300 flight is peanuts when you are considering spending six figures on a home. 

These people overwhelmingly live by the belief that the eye-popping on-paper cap rates and cash-on-cash returns they acquire most of their properties through are the tickets to generational wealth they are passing on to their children.This turns out to be an illusion. 

what are the big ticket items driving that budget - foundation, roof, concrete, mechanicals, garage repair? 

When a flight attendant is giving instructions for emergency just before takeoff, and they start to talk about the oxygen mask, why do they say to put yours on first...then your children? 

You can periodically take a flight from Canada to check on your Chicago portfolio and then a direct flight to Huntsville Alabama.   

Utility bills: Water, Sewer, Gas, Electric (at least two years of monthly statements) (or recap report from provider showing usage and cost) Bank statements showing deposits for last twelve months (optional) Phone system documents (y2k compliance letters) Computer systems (y2k compliance letters) Fire System inspection reports and y2k compliance Property Tax tickets for the past three years (real estate and personal) Litigation History: details of any past or pending litigation (if none, then affidavit from owner) pre-closing Engineering Inspection and Survey Environmental Inspection and Survey: Key Issues: Asbestos, Lead Paint, underground tanks, wetlands Environmental Phase One: An Environmental Phase One (1) Assessment is an inquiry conducted to determine the environmental status of a property or facility in connection with a real estate property transaction.

Delayed Financing may be your ticket, as you get best of both worlds.