Lesson: don't do illegal things like rent out units that aren't up to code  - some people with paid off properties try to be cheap and do things like this or do under the table rent so they don't report rental income to the IRS.

I would love to get his thoughts on how that is going and if the headache is worth the uptick in income. 

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.

So, typically you as a principle have to personally guarantee the loan.

We did not need help in deciding what our investment niche would be; we needed help in creating and implementing a tax strategy plan for a married couple composed of a high-income earner and a real estate agent and business owner.

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.

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.