My biggest recommendation is to write down all of the "Use cases" you would like and then determine which software actually works better for you personally. 

Our biggest problem is that it is booked so often we never get to use it.

I would venture to say all of the frequent tax sale experts here on BP can tell you story after story after story of land minds people buy at tax sale, that may end up being the biggest headache of their life.   

And don't assume that the bigger the developer the lower the odds that this happens to them, as I heard that one of the biggest developers is in that situation.Finally, while I usually will answer any questions, I won't it comes to my own project, I can't respond for the following reasons:1.

The max Uncle Sam allows is 50k if you haven't taken a TSP loan in the last year.I've seen both good and bad experiences with this but at the end of the day it's no different from any other type of loan, you are just your own bank in a sense.The downside or risk is that you lose your job, your property isn't cash flowing, are unable to pay back the loan, and your retirement account suffers since the loan essentially turns into a withdrawal.The upside or best case is you have the loan for less than a year, your BRRRR pays off the loan, and you pay yourself interest 5% interest.The opportunity cost is if the stock market goes up 20% and you were only paying yourself 5% interest you'll miss out on the excess returns. 

The biggest pain point many face is when they are stuck in between where deals are not big enough for the larger check writers but the  equity needs surpass the friends and family network of relationships.

Yes I've read that the only downside to doing it that way is the possibility of triggering the sale purchase clause, however as you said maybe it is more common than not.

@Jacob StraussenTerm is essentially a commodity biggest difference you will see is if you want to have options to convert to perm that's when you would want to do more research and really get carrier specific.  

For context, I have a business degree in marketing (not good I know) and work for the biggest single family rental company in the US doing entry level customer service.

Dear Landlords, As an investor, my biggest asset is my property.