I am not a lawyer or tax professional, these are just things I've heard.

New BP member here looking to connect with other South Florida real estate investors and professionals. 

HOA fee - If HOA fees are not paid, business will incur fines, so it is necessary to make the profit in the business.8) Marketing expense and advertising9) Cleaning and maintenance10)Commission (Expenses like commission, abstract fees, recording fees to obtain your mortgage are not deductible but rather capitalized )11) Insurance12)Legal and other professional fees(Tax preparation for business, not personal part)13)Management fee if applicable14) Points- you generally cannot deduct the full amount the first year but have to deduct them over the term of the loan.15) Repairs (Note always do repairs rather than improvements to rental because repairs are deductible right away and do not have to depreciate over few years as done for improvements.

I'd argue there ARE opportunities in college towns like Blacksburg, but the real opportunity is for rentals to the graduate/professional, which is underserved in our area.

You must become that professional.

If the latter, how would you approach an increase like that to someone you know on more than just a professional level?

I dont know your intention, so talk to professional. 

, you can reduce your risk of getting a "professional tenant" who knows how to abuse the system. 

It is ordinary and necessary for real estate investors to notice wear and tear from year to year and claim "depreciation" on their properties.The rule that your accountant is referencing to is the "real estate professional status" which allows you net losses from your rental activities with your other income if your adjusted gross income is above $150,000.

Of course you have to qualify as an accredited investor for most, but if you do qualify it gives you the opportunity to get into bigger deals/more units that you otherwise would not be able to accomplish or afford on your own.You'll also be a limited partner in syndications, i.e. no active role in managing the property, so you'd have to be okay with that as well.Just food for thought!