It is a 1 bedroom "loft" style townhome with a lot of cool features, but the reality is unless I undertake a major renovation, it will always be a 1 BR and I think its value is limited from a rental and sale perspective.Any thoughts?

@Kim Meredith Hampton Regarding Page 10 of the lease provided by the FARBAR:  http://dewittlaw.com/commercial-litigation/3701/li...Since the lease is preempted by FL legislature, this ties the hands for the kinds of lease provisions which contemplate move-in fees, redecoration fees, smoking penalties, security deposit fees, etc. 

And an extra level of attention to detail & double checking that the surveyor must undertake, lest they suffer the dire consequences of missing something, which might include, but not be limited to, law suits, force choking, insurance claims, damaged reputation, etc.

I have a rule that we always follow: you need at least 3 contractor bids minimum for each deal you're looking to undertake.

Another point is that the really old houses were not built to be super tight, and sometimes using closed-cell foam makes them a little tighter than they can handle (like having one to many ;-) ) and you have an acceleration in the rate of deterioration.Insulating and air sealing are disruptive undertakings - the degree of disruption can vary and will act as a limit of the degree of insulating or air sealing you can obtain - but in our experience, you can achieve 40 - 60% of the desired/possible improvement with minimal impact.

This will be our first major undertaking in terms of investment properties. so I'm even more paranoid that I've missed something since we've worked so hard to get this going.

In addition she has many rentals of her own, so knowing what projects to undertake that will generate the largest ROI s something that she can not only guide you on, but has done many times on her own.

This is a big undertaking for a new investor.  

So unless you know for sure that the OP is undertaking a rare few of a vast number of investing tactics, your whole issue with trying to convert income taxed at marginal rates to income taxed at capital gains rates completely falls apart.  

So was it your business that was undertaking the commercial loan, or your personal self?