Brandon Turner's Rental Property Investing book is an excellent primer to understanding the happy path for purchasing a property - however in this market it really comes down to having bulletproof assumptions on rents/taxes/R&M/etc. as with rates as high as they are/inventory as low as it is, there is less cushion in your returns if you analyze properties with bad assumptions.

I prioritize appreciation, tax benefits (rental property expenses, depreciation), ability to use leverage, and passing on generational wealth with real estate. 

Your equity doesn’t matter in the taxes or decision.

In order to defer all of the tax you must purchase a replacement property that is at least as much or greater than what you are selling for.

The article also fails to mention that overall transaction costs can actually be higher in countries where commissions are lower because the agent plays a different role, and due to needing to pay a lawyer for paperwork that agents complete here as part of their job (called a solicitor in Britain) plus VAT taxes and other closing costs need to factored in on top of the sales commissions, which we don't have here, overall costs can actually be higher even if commissions are lower. 

. ==== Projected Income ====**Off Season**-$4,000/Month Rent Period: September - May (7 Months) Projected Income: $28,000**Summer 1**-$8,000/Week Rent Period: June (4 Weeks)Projected Income: $32,000**Summer 2**-$8,500/WeekRent Period: July-September (12 Weeks) Projected Income: $102,000**Optional** (Basement Apartment)-$2,000/Month -Rent Period: Year Round Projected Income: $24,000TOTAL PROJECTED INCOME: $186,000 ==== Operating Cost ====-Mortgage: $84,000 ($7,000/Month) -Utilities: $36,200Gas $6,000 ($500/Month) Electricity $6,000 ($500/Month) Internet $2,400 ($200/Month) Garbage $5,000 (Estimate) Pool $4,000 ($250/Week)Landscaping: $4,000 -Mowing: $2,400 ($150/Week)  -Clean Ups: $1,600 (Spring & Fall)-Weekly Turnovers: $8,800 ($550/Week)==== Legal Cost ====Summer Rental Fee: $20,100 (15% of $134K)Sandwich Rental Tax: $6,855 (15% of $45,700) NET PROFFIT: $38,845.00

I would reinvest in a another property and use a 1031 exchange to detour taxes.   

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

A FHA 203k Loan is where the purchase price and rehab costs are rolled into a single loan.Assuming you have a respectable FICO you can buy, with a FHA Loan (3-5% down, a 30 year amortization schedule, and a residential loan rate) AND because you closed personally, you will not have Asset Protection, in the form of closing in the name of a LLC/ LLC taxed as an S Corp, or an S Corp.

Also, the tax benefits of the buy and holds help offset the increased tax consequences of fix and flips.