Tax considerations involve a lot of personal, specific considerations so you are on the right track going for a CPA (make sure they are familiar with income properties and short term rentals).STR is a business and involves "active" income versus "passive" income associated with typical long term rentals.A few general things:1.

It involves some investment but might pay off in increased property value and rental income down the line.Also, assessing the market in spring (#3) could be beneficial if you're looking for a strategic time to sell.

I am aiming to overfund the initial purchase if I can to cover property, repairs, assumed mortgage cost for months of no income (assuming 6 months max), and any variance.

Under that assumption, 1-3 are all considered earned income when received.4.

I could get more ambitious with the renovation and make 4 total apartment units with 2 approx 800 sq ft. units on each floor to get a lot more rental income. 

Short term capital gains is your ordinary income tax rate and long-term capital gains where you hold the property a year or longer is considered long-term capital gains is in as taxed a lower rate.  

Our goal is to (eventually) have a second property where we can spend time at our retirement, and that can generate some income as a short-term rental for a portion of the time when we're not using it. 

My current property manager doesn't instead sending a monthly ledger with the month's payments (company name, pay date, amount) as well as monthly income/expense statement.

See example below: DSCR < 1 Principal + Interest = $1,700  Taxes = $350 Insurance = $100 Association Dues = $50  Total PITIA = $2200  Rent = $2000  DSCR = Rent/PITIA = 2000/2200 = 0.91  Since the DSCR is 0.91, we know the expenses are greater than the income of the property. 

I am responsible for a pretty large mortgage payment and only my employment income to pay my mortgage in all the bills.