All seasoned investors know who to run the deal by before they write and that person would always fit my five point definition of a deal killer.

Do you have any contractor recommendations that you think could be a good fit?  

Engage an investor-focused realtor/broker in your preferred market (this is not a residential realtor) and start 'tire kicking' the market and properties that fit your criteria.

I designed a little U-shaped kitchen to fit right in the space.

Hey @Jordan Northrup check out Buildium, it may be a decent alternative and fit the bill for what you're looking for.

The best market for YOU, is the market that fit's YOU; you're situation, your preferences, you're resources, your knowledge level, you're risk aversion and about 40 other personalized factors to you. 

Instead we recommend all our clients to secure their properties as they see fit.

If you want predictability, value hard assets, and like the tax advantages, then investing in a real estate syndication may be a good fit.

Most of our investments we look at IRR (time value of money) to determine which investment is a good fit for us at this time - which factors in returns, risk and time of investment - is it a short term investment we want to get appreciation play or long term fixed income investment.

Does attic fit the heater there with 3 feet clearance and also duct work.