Far different from buying and "maintaining" a property in hopes they market forces improve the value.It's the same as purchasing a stock after analyzing that market and charts.The other factor is inflation, the other thing we have no control over.

In the latter case, I would still use QB to enter info provided by the 3P servicer and to maintain my general ledger for the lending business.

Which will also depend on the neighborhood.You want to, "rehab/maintain to the Neighborhood".Most investors go overboard on their first rehab and waste a decent amount of money.

Typically if demand increases and supply is maintained prices go up. 

Theyre expensive, but you wont lose your home to foreclosure unless you move out, stop paying taxes/insurance, or fail to maintain it. 

Concentrate on increasing your earnings rather than on not paying off your debts.

.• Use some equity from the sale to make this transition smoother.I’m torn between maintaining our current home as an asset and buying  a new smaller house to use as a rental after we move back in versus simplifying and focusing on a single upgraded property Considering factors like market trends, potential equity growth, and quality of life, which path do you think would be most beneficial?

My concentration for AirBnB is Gettyburg PA and Cape May NJ. 

Leverage and invest at 40x $100 000 properties ($20k down + $5k closing cost, 30 yeas fix rate loan) with a return of 10% where you have better asset protection (my keeping lower equity and higher bank position), you are hedge against inflation (agree with me, in 30 years $1 000 000 purchasing power will be less compare than $1 000 000 today) Here is how looks mathematically:1. 10% on $1 000 000 (10x $100 000) = $100 000 / annually - No interest tax deduction- No loan paydown benefit2. 10% on 1 000 000 (40x $100 000) = $400 000 / annually - debt service + full tax benefits+ loan pay down+ hedge against inflation for 30 years+ better asset protection (by maintaining lower equity  position)   + (not guaranteed of course) if appreciation happens, it happens on the all full asset amount, example:If appreciate 10%:In case "1" you will have 10% on $1 000 000 = $1 100 000In case "2" you will have 10% on all 40x properties (40x $100 000 = 4 000 000) = $1 400 000As far as cash flow, as long you buy "right" CAP 8% and higher you will have stronger cash flow on leveraged asset + all additional benefits.

A house hack could definitely be a good first step, allowing you to build wealth while maintaining your lifestyle.