With so many “alternative” qualifying programs out there, there really has to be something other than “under 2 years employed” or “doesn’t show all his income” for the buyer not to be able to obtain institutional financing, and hence be willing to spend $250k for a $200k house. 

@Mathew Morford what type of investing strategy are you planning on employing?

For example when a large employer in a small town closes up shop taxes may continue to go up at the same time as people move away or can't afford rent forcing rents downward.

Understand your financial capacity to invest in a property and estimate your monthly expenses accurately.Kansas City is rapidly growing- lots of employment opportunities and housing demand.

Indianapolis does have a diverse job market, low unemployment and companies moving there (FedEx and Eli Lilly are two major employers and many hospitals). 

At one condo I owned they kept the monthly fees low but during my ownership had a "special assessment" for new roofs and later had a "special assessment" for paving the parking lots. 

Im a first time home buyer, no existing debt, self employed, bring in average $4k monthly, looking for a conventional fixed rate loan in PHX or surrounding areas.

Just to add a bit more, if you are looking for tax benefits like they have in the US ( for example where you can deduct expenses against your employment income in certain cases), unfortunately we don't have that in Canada.

I have access to my employers subs for plumbing, electrical, and we have some finish guys for rock/trim.   

After a thorough set up with them we simply email them receipts with a note for what it was for/what project and they allocate it into the right category.Now if you have the capacity to learn quickbooks or employ someone who is versed in it then that is your best bet.