If the STR strategy is the only strategy that makes the property pencil, be sure to purchase in a market where the use is allowed, the use requirements are protected by in place permitting and licensing and the permissions are transferable through a sale.

I’ve had to change my strategy due to my city being a high market.

House hacking is one of the most popular strategies you can take and it can be a great way to build wealth and generate passive income but it's important to have a long-term plan in place.

.- Condos are typically closer to very busy areas like city centers (while single family and multi-family are further away / in suburbs) which, in the case of a buy-hold-rent strategy, means that the investor will have more traffic / demand.- Smaller properties are usually easier to off-load (more liquid) because our society is seeing very high levels of migration (people travelling or moving for work constantly) / people less inclined to partner / have families / people more focused on work / and pied-a-terre concept.- Condos are much easier to maintain internally than larger homes.- 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!

In terms of strategies, you can do something other than a full gut if you're more conservative.

.- 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.

I think the first question you should focus on, is what your intended investment strategy will be.

@Jessica Morrisonwould need way more info... you haven't provided geographic location / area, numbers, strategy, financing info...what does your agent think?

I'm still learning about different strategies, markets, etc. from podcasts, books, and the learning articles here. 

@Ryan Larsen what @Nicholas L. states is pretty true.Being a PM is NOT a high-paying, often not even a well-paying job.If you're set on that strategy, start calling up local large apartment complexes and asking if they are hiring.