Whether you need a CPA with just three rentals depends on the complexity of your situation and your comfort level with DIY tax prep.If things are pretty straightforward, you might be fine with tax software for now.

Purchasing subject to allows you to (1) buy a property and pay a lower rate (3-4%) that was in existence when the loan was originated, so cash flow will be better as well as equity buildup; (2) not have to qualify for the mortgage saving time, expense, and allowing property purchases in greater number than otherwise and (3) no personal liability on downside (4) no debt added to your PFS.  

https://www.biggerpockets.com/forums/51-tax-legal-issues-con...

Since you’re assuming this debt as part of the purchase, understanding the exact amount is critical.

Hi Jon from Boyertown, PA-You and your fiancé are interested in buying your first short-term rental and wonder profitable areas to purchase with a budget up to $500,000.I would look at places along the west coast of Michigan, Grand Rapids, Kalamazoo, and near Ann Arbor, MI.It is important to understand the local STR regulations in each community and partner with a property management company that can help your navigate that and manage it well for an excellent guest experience.Don't forget to look into bonus depreciation and doing a cost segregation study to increase the tax benefits of ownership and if you "materially participate" in the management of the property per IRS guidelines it can offset active W-2 income which most real estate cannot.To Your Success!

Sellers can avoid paying transfer taxes to the county, while buyers are spared from facing significant property tax increases.However, it's important to note that lenders typically only approve these loans for properties with five or more units.

I can buy a 2-4 unit with 20% down vs conventional can only buy a 2-4 INVESTMENT property with 25% down 4. there are options where DSCR loans dont repot to personal credit, helps in not having to show a bunch of paperwork or not one person in a partnership has to carry the debt5. way less paperwork to close on this loan type vs a conventional loan. we care about the income of the property you're buying and it's ability to service the debt of the property whether we use long term rents income, lease income, or air dna/bnb income.6. easily buy in partnerships, add people to your operating agreement, its as easy as that so bring partners into a deal. helps with scaling and raising capital or getting partners involved7. gift funds allowed to close on these as well, and like I said earlier, there's only a 10day seasoning period of funds with some lenders so that means you can literally have a private money lender deposit money into your account 11 days before closing, and you can use those funds to close!

What if you're a cardiologist with no debt and making $250,000 annually?

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

Just transferring it gives you zero protection - the reason why it never comes up is because no one can name ways you get sued when you have a good insurance policy so its a mute pointSo long story short, you are wasting money transferring it to a LLC is my personal non legal non tax opinion.