@Cameron Belknap FHA loan rules in HUD 4000.1 mention not counting the basement as part of the Gross Living Area; however, part of the FHA requirements found in HUD 4000.1 includes a section on “converted spaces” which states:“The Appraiser must treat room additions and garage conversions as part of the GLA of the dwelling, provided that the addition or conversion space…is accessible from the interior of the main dwelling in a functional manner; has a permanent and sufficient heat source… and was built in keeping with the design, appeal, and quality of construction of the main dwelling.”Furthermore,“The Appraiser must analyze and report differences in functional utility when selecting comparable properties of similar total GLA that do not include converted living space.

Also remember, CAPITAL gains are not an additional tax, it's a specified rate so it's not a second tax. 

Rent will increase and addition $50 after that.

Plan - close in September, renovate the empty and ask for an additional $70 from that one, an additional $50 from the one downsizing and remain the same on an efficiency. 

We needed additional income as we were purchasing our home, so I got a job at a financial firm (had to inactivate my license) and have been there ever since.

depending on your lease, the original tenant may be harboring the other tenant and be violating, I may consider discussing with the tenant (assuming the lease specifies who can live there for how long) that they are in violation of the lease, and you can remidy 2 ways, volunatilly terminate the lease and resign a new one with the additional tenant, or you can go down the eviction route. 

In addition to spreadsheets, I was curious if anyone uses a checklist when analyzing properties; a series of questions, reminders, and information to acquire as a guide you use? 

They are definitely hands off, 1031 exchange eligible, and have been a wonderful planning tool for a lot of folks...including those that still own/manage real estate in addition to their DSTs.  

From my previous learnings, my initial strategy is to invest in a duplex and "house hack" while gaining more experience to invest in additional properties. 

Additionally, my parents are giving me the option to receive a lump sum payment to go toward possible rental property purchases.