Start-up costs are also deductible but are amortized over 15 years with a limit of 5k.Start-up costs have strict rules and your case might not be the same as this one.Case Summary:Timeline line of eventsStarted investigating property: FebPut first contract (canceled): MayBought first property: December 30thWhether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business:Whether the taxpayer undertook the activity intending to earn a profit;Whether the taxpayer is regularly and actively involved in the activity; andWhether the taxpayer's activity has actually commenced.On the basis investor testimony, we may assume that he undertook this activity to make a profit and that he regularly and actively engaged in it.

I self manage my units so my views are more related to the actual work of property management rather than communicating results to property owners.The most important factor in successful property management is not a personal quality or trait, it's having EFFECTIVE processes in place to support the business.

Liability will be a huge factor, but there are other considerations that a licensed agent can discuss with you.#2) You can, and should always, vet the financial stability of any insurance carrier on A.M.

How passive and how safe these other options are, are also important factors to take into consideration.

The next factor is since you are looking to use that towards a down payment for your next investment you will need at least 20-25% down payment.

Factors to consider include proximity to campus, tenant turnover, seasonality, property management, and financing options.

You have an 8% vacancy factor, but does that include bad debt? 

You also risk:1) Committing mortgage fraud by misrepresenting the property and/or how you're using it.2) Exposing yourself to liability if the 3rd renter discovers they are in an illegal unit.3) Voiding your insurance.

There are many factors to consider, I drop some here: 1) being new, need to build your reputation and have no repeating customers2) Miami has had an overflow of STRs buildings and "illegal" inventory: investors who bought new condos allowing STR with loans to pay, tend to lower the price to get bookings.

Are they doing everything possible to expose properties to the broadest possible market?