I'm a software developer and have worked with a bunch of REI companies that use Carrot. 

We have a software program we use for managing the units that has all our numbers in it, but I haven’t utilized anything like quickbooks yet....

Anyone using rent manager as your property management software?

I use Transunion which is built into my property management software. 

My background is in software development and web application development, so I know I can assist with technology related questions. 

Understanding market conditions is key, and getting to know the little things that have huge value influences, now if you have a cookie cutter home with plenty of sales it pretty easy, but if its an oddball with little market activity, it can be kind of a crap shoot, go with your gut and be conservative on the numbers, its way better to be off on the low side than way over valuing. good luck!

I'm a software developer looking to develop a suite of solutions for landlords with a smaller portfolio.

Now that my property  is worth more because it is shooting off more income (on larger multi-family and commercial, value is strongly related to NOI - hence, you can significantly effect capital appreciation with minimal broad market influence), I can further raise the IRR by cashing out a refi or selling for nice profit.

Only you can tell if this is a good deal, and if you don't know, I would suggest you pull back and better define your retirement goals, which will influence your investing goals, which will determine your buying criteria.

From that point on, should you need to track your business transactions thru an app/software, you will only need to refer to the business account since you already knew that you are separating them from the beginning.