I've done more foolish things with $20,000 in my short life, so I'm inclined to just pull the trigger on this one.I'm all ears, people!

Agents are definitely more inclined to invest in your services if the service will help generate leads. 

If you can do that, I'd be inclined to call it a repair in both 2015 and 2016 rather than a capital improvement under the new Final Tangible Property Regs.Also, how much is the repair going to cost you, what is the total dollar value of all repairs completed for this property throughout the year, and what was the property's purchase price plus improvements?

Given that she signed a 3 year lease, I'd be inclined to spend the $159 and keep her happy.

Few homeowners pay attention to the HOAs, so boards may be dominated by zealots or by people who are not inclined to question the management. 

Willing to do some rehab work but less inclined to an all-out gut job while living there.It would be nice if this circumstance could springboard into successful real estate investing ongoing but I do not yet know how serious I will be about it as time goes on so I'm a bit cautious.

If it is their space I would be inclined to allow more leeway through restricting volume/size. 

My inclination is neither should be included in my assessment of CR and they should be included in COC as they would reduce year 1 COC but not subsequent years COC.  

Three years in a treasury as opposed to a 7.5% CAP multifamily is ostensibly a self inflicted tax....if that spread were considerably less, I might be more inclined to pay the tax and move in to the treasury.  

Maybe you have the time or inclination to work on one needed task with this asset.