How do people then generate a monthly rental income? 

Thanks to the Cost Segregation Study, the property investors accelerated the depreciation that the first year depreciation was approximately $182,900.The use of the accelerated depreciation strategy helps real estate investors to reduce the tax liability immediately which therefore increases their bottom line due to the offsetting of income.

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. 

Current income is only 1100 a month.

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.

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. 

If don't need construction funds can just do a bridge loan no income and no doc with 30% down for upto 24 months interest only 

Renting offers steady $4,000 monthly income, long-term property value growth, and potential tax benefits.

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.

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.