I've even thought of buying a rental house to offer to a full time employee to move to this area but I'm not sure if that would just create more headaches in the long run) Employer responsibilities; payroll taxes, administration and audits.

However I understand we'd be at high risk of audit if we go through with it.PS.

I do not use PL or Hospitable but have had similar issues with our software and integrations. 

There's software that can tell even which blocks has the highest appreciation per zip code. this is for rehab or buy-and-hold long term.The inside factor that really makes higher appreciation is good school districts as parents wouldn't need to pay private schools for their kids. 

You can easily get audited and caught for mortgage fraud for putting in a 12 month lease.  

It doesn’t take long with tax software but if you can save current tax dollars today, many think its worth it (not considering the strategies to avoid recapture as well).

Hostaway is a short term rental software but with enough finagling you can get it to work for mid-term as well.

@Sumiya Mahmud Have you looked into some of the self managed software options?

Curious if anyone has had any luck managing all these aspects in one singular software?

It should be handled by your tax software or, better yet, by an accountant.You also have an option of paying the entire capital gain upfront, which is usually not to your advantage, however in some situations it could be.