In our experience in Denver and Colorado Springs with midterms, it take 12-18 months for the extra income from it being an MTR to pay for the furnishings.

Understanding and taking advantage of the variety of tax credits boosts the return on your property and allows you to be part of the move to conserve our nation’s historic treasures.When rehabilitating or investing in the rehabilitation of an eligible historic or non-historic building, you may be able to take advantage of one or both of the historic tax credits: 1) Historic Tax Incentives and 2) Historic Preservation Tax CreditsYou can receive a federal income tax credit equal to 20% of the costs associated with rehabilitating the building.

Anyone can declare real estate losses against their active income if their income is under the AGI threshold but only someone whose PRIMARY profession is designated to be a real estate professional will be able to offset active income. 

However, the nights they cancelled have already been completely filled by other guests, so I didn't really lose the opportunity to generate income. 

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.

Current income is only 1100 a month.

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.

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. 

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.