Keep in mind - operating the STR to it's peak performance will require diligent thought and effort to best generate reviews, drive up the nightly rate and occupancy, and maintain an edge over your competition! 

If you are familiar with the software that you are using and can generate reports(profit and loss + Balance Sheet), then it shouldn't matter what software is being used.If you need assistance making adjustments, then it helps to use the software that the CPA is most familiar with.I personally think Quickbooks Desktop or Quickbooks online are the most familiar by CPA's.Best of luck.

This could be a long-term investment that generates income over time.3.

Still, the main goal of my investing and that of my mentoring clients is cash flow to generate a passive income flow that ultimately leads to reaching the Time Freedom Point at which one has the choice to exchange time for money (JOB) or live your passion regardless if it makes any money.In 2022 we have all seen the FED increasing interest rates and along with it, mortgage interest rates have gone up a lot.I wonder what the BP community thinks about the future of interest rates, especially for financing our residential property investments and what you would do or accept regarding cash flow.

Make sure you feel comfortable with the length of the lease and that you're confident you can generate enough income from the property to cover the rent and down payment payments.Terms of the contract: Make sure you fully understand the terms of the rent-to-own agreement, including any penalties for breaking the lease early or missing rent payments.

Sure, some modern building methods are far superior to what was used in the past, but lots of building methods used today aren't nearly as robust as in prior generations (ask an experienced GC).....Additionally, a new house is still in its "growing pains" phase, and a lot of serious problems can emerge in the first few years of ownership--e.g.; foundation/structural settling, improper water diversion systems creating rot, etc.

The goal is to replace my 9-5 and to create generational wealth for my family and me. 

You are thinking way too far in advance.An investment property purchased now in most likeliness will not be generating positive taxable income given high purchase prices and high interest rates.Have a talk with your CPA to ask them what your tax exposure would be if you mentioned to him your purchase price, monthly rent and basic expenses like insurance, interest and taxes.Best of luck!

If you purchase and it is that generation, assume if it is on sand that it is beach sand.  

With deferred maintenance taken care of you should be able to raise the rents, a bit at a time, and have an income generating asset to hold and benefit from for years to come.