This process is extensive, requiring community engagement and approval from the City Planning Commission and City Council.Given the predominance of multifamily residential properties in your area, there may be a precedent for such developments.

We want to travel and invest and are considering converting this short term rental to a long term rental to avoid sales tax, paying utilities and general management of the property. 

I pay no utilities and these are all one year leases.2) THEIR CREDIT RATINGCollege students almost always pay their rent.

The other half of the accounting records is coming from online purchases, utility payments, etc etc where they are sending you an email. 

Most investor utilize short term hard money debt to scale their flipping operations where the lender will fund 80+% of the purchase price and the rehab budget which can allow investors to work on multiple projects at once.

Utilize a 1031 Exchange: Under IRS Code Section 1031, you can defer capital gains taxes by reinvesting the proceeds from the sale into a similar “like-kind” property.

If your credit is decent then I would utilize your cash as leverage to leverage:1.

Trying to manage a $1M Airbnb rental while it sounds good you got $6500 in bookings you still have significant costs to operate it with maintenance repairs, utilities etc.

If you're planning on utilizing a self-showing model with cameras you'll need to make sure you disclose to prospective tenants viewing the property that there are cameras on premise.At scale, we've coordinated 160,000+ on-demand/self showings with smart lockboxes over the past 5 almost 6 years with very few issues.

However, if you have a more extensive portfolio or plan to become larger in the next year or two, I would look for a double-entry system that allows bank reconciliations.