The accounting software that you choose should not impact your relationship with your accountant as long as you can provide them a report that is easy to read and understand.I would suggest, if possible, to change softwares at the start of a year as it would make things easier.Furthermore, make sure you to carryover all balance sheet ending balances to your new accounting software.Best of luck

If you think there might be the possibility of development raising the value in the future, you could try renting out the property to others for non-intrusive uses - parking, roadside vendor, etc. 

My question is: Is this house better off being rented long term for tenants or should I gravitate toward a midterm rental for possible traveling nurses or traveling professionals who want a cleaner, more up to date space, closer to downtown?

You've possibly stated in writing that you (may have) violated several laws ie. working as a property manager w/o the proper licenses etc. 2.

I haven't reviewed the Standard Lease Agreement yet, but all I need is the right to sublet, and possibly some negotiated capital responsibilities (owner pays for repairs over a certain amount or split responsibilities on certain expenses).

Then after that, you have more trusted contacts, then diving into world is more possible

I know people who do STR in their house, but it's as private as possible.

Hi @Tim Holt I think in general house hacking is usually a good move because it gets you off the sidelines and into the game with the most favorable financing possible (30 year fixed).There's a lot of value in getting started today vs waiting some undefined number of years until conditions are better, which could be a long time from now, because real estate is a business and the sooner you start actually learning about that business, the better.With all that said, I always recommend that people analyze any potential house hack as a pure investment that they aren't going to live in, because someday they may want to move out and you should know up front (before you commit) whether you're going to be able to do that, or whether you're overpaying and will be stuck in the property unable to move out because it'll be cash flow negative if you do.So you had it exactly right when you wrote, "the property would need to cash flow when I move out and rent out all units."

Instead, prioritize strategies that stretch your resources as far as possible while building experience and momentum.

If you've got evidence of them in the past, they could come back (and yes, I've had termites in two of my slab foundation homes, so it's definitely possible and happens, at least in my area which is NC). 4. $25k for helical piers sounds a little steep, but it's been a few years since I saw a quote for that, and of course it depends on how many you need.