It depends on Johnny's tax rate, and how much employment income he already has. 

https://www.biggerpockets.com/forums/530/topics/1056436-clearing-up-confusion-on-tax-treatment-of-short-term-rentals

.- Property receives one set of taxes- Both houses are approximately the same sq ft. (1300)- Two single-family homes, not attached (two different addresses)- Property size 0.45 Acres- Township won't allow subdivision unless each house sits on 0.5 acre lots- Will reside in one house upon purchase, and will rent out the second house- One house currently rented out for $1,400 a month with a one-year lease- Purchase price $260,000Looking for ideas or best ways to finance this type of property!

Like when I did my last one, the study was going to cost $1600 and the benefit of it was $28,000 in tax savings.

There are already risks, don't make legal and tax issues be another risk.

@Rajshekar Manaliker I’m here in south Florida and we’re still moving and shaking with a good amount of incoming residents from income tax paying states

There a ton of pitfalls that can just crush you. from bad tenants from hell to city regulations that are impossible to figure out to taxes to bad rehab jobs etc.

Obviously 1k is not enough to cover the transfer tax and Sheriff's fees... 2) I thought Sheriff's sales were exempt from transfer tax in PA?

We are interested in making use of the STR tax strategy to offset our W2 income this year (work 100+ hours, average rental less than 7 days, no one else worked more than us).But1) Can we only keep it as short-term rental for 2024 collecting minimal STR rents and convert it to LTR in the following year (2025).

Bu equally important that the seller is current on their property taxes.