You should split the income/expenses for the building after you each paid fair market rent, not each take one unit  Good luck  

From a tax angle, that two-family is a solid start because you can use depreciation to reduce taxable rental income, and your cosmetic upgrades may qualify for deductions or depreciation (like someone above mentioned, definitely look into cost segregation), depending on the work.

If you place it on Airbnb, get guests in, and complete a cost segregation study, you can take bonus depreciation against W2 income as long as you meet the hour requirements.The key parts are: buying the property, putting it in service, tracking your hours, and getting the cost seg report done in time.

You asked about short-term rental property demand and mid-term rental property demand in other areas besides yours and thoughts on managing these properties.First off, short-term rentals are a great property class to own, especially if you "materially participate" with 500 ours in the management of your property for the IRS to consider it an active investment and able to write down your active or W-2 income with the expenses, bonus depreciation, and cost segregating the property for additional depreciation to reduce your income taxes.There is short-term rental demand in many communities in Michigan because we have so much coastline and natural beauty as well as university, business, and hospital stay demand.

My plan has been once i got situated with a stable source of income to start investing in rental properties.

Most of the inquiries are from people with borderline or poor credit, high debt loads, or income levels that don’t realistically support the rent.My early experience with long-term renters on the Cape is that there’s a very limited pool of financially stable applicants, and a large number of people looking for rentals they can’t realistically afford.For those who own long-term rentals on Cape Cod (Dennis, Yarmouth, Harwich, etc.), what has your experience been?

Since you no longer live in Wisconsin, you may face state income tax considerations both in your new state of residence and Wisconsin, especially if you generate rental income or take deductions on the Wisconsin property.You could also explore passive investing with partners in larger properties to grow without managing everything yourself and these don't have to be local.

This dividend income will help you qualify for loans eventually, supplementing your W2/ day job income. 4.

It’s clear: Philadelphia is poised for continued growth and popularity, with a dynamic market that offers a unique blend of affordability, resilience, and upside potential—making it the best Northeast market to invest in over the coming years.Case Study: 5000 Florence Ave, West PhiladelphiaHere's a concrete example of why Philadelphia offers compelling investment opportunities:Current Income & Rents:The property generates approximately $48,000 annually.

@Gary Tucci,A cost segregation study can definitely be worth the investment, especially with 100% bonus depreciation.Since your short-term rental (STR) is likely non-passive due to your material participation, the bonus depreciation can offset other income, including W-2 income.