.- Condos are easier to manage as Air B&B than larger homes.- In the case of multi-family properties, sharing a home with two or three other families where everyone knows everyone can create issues if they don't get along as the close proximity doesn't allow for any privacy.Happy to connect with you and speak in more detail if you are interested in Massachusetts!

Sure, managing what you've got is important, but without a deal, you're just spinning your wheels.Now, when it comes to buying up properties, multi-family ones are a whole different ball game compared to single-family homes.

Any midterm rental property managers? 

I currently work as a Relationship Manager in Canada but I've been considering moving back and establishing the real estate investment portfolio that I've always dreamed of. 

In my area up to 4 units will be serviced by the city but as soon as I go over 4 now I need a dumpster and a private trash company which is an added headache around site design / cost management /securityCosts/requirements for driveways parking.

Myquestion is this: can I create an incorporated property management company to funnel my current rental income through, then pay myself a W-2 salary from that company in order to raise my W-2 income so that I qualify for the mortgage on the new property?

Even if you self manage your underwriting should include this as it is effort and takes time.My thought on the ADU is before you proceed be sure that you understand the value that will be added by the ADU.  

However, ensure you conduct thorough research on the Indiana market, including economic drivers, rental demand, and property management options.Consult with Professionals: Given the complexities of 1031 exchanges, out-of-state investing, and retirement planning, it might be beneficial to consult with a financial advisor, tax professional, and real estate expert who can provide personalized advice based on your specific situation.Retirement Income Planning: Consider how this investment aligns with your overall retirement income plan.

.- Explore strategies like 1031 exchanges to defer capital gains taxes.Deductions and Expenses- Know eligible deductions: mortgage interest, property taxes, insurance, maintenance, and management fees.- Maintain detailed records of all real estate-related expenses.- Use cost segregation studies to expedite depreciation of your properties to offset large income gains.Entity Structure- Choose appropriate legal structure (LLC, partnership, or S corporation) with consideration for different tax implications.Tax Credits- Explore available credits, like energy-efficient or historic rehabilitation credits.Qualified Business Income (QBI) Deduction- Check eligibility for QBI deduction, providing up to a 20% deduction on qualified business income.Record Keeping- Keep accurate and organized records for tax compliance and audits.State and Local Taxes- Consider varying state and local tax implications, including property and income tax rates.Tax Planning- Engage in proactive tax planning, consulting with professionals for a comprehensive strategy.Tax Changes- Stay informed about changes in federal, state, and local tax laws affecting real estate investments.Remember to consult a real estate tax professional for personalized advice based on your specific situation.

Additinally, most self managers actually lose money through lack of market knowledge and poor management practices.