(cash flow, tax benefits, potential for appreciation) Whats the timeline?  

After looking at a lot of them, I would probably only be interested at 40 rooms or more due to staffing levels. 

. ==== 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

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

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.

Great point about state income tax, @Jay Hinrichs.

Expenses: What are the operating expenses, including taxes, insurance, maintenance, and reserves?

There are a lot of LL advantages due to the low vacancy rate.

I’m told taxes and insurance is lot and will rise each year and cash flow is hard to come by.

This is because the dwindling cash flow due to the increased rates has resulted in higher cap rates.