My wife and my professional careers offer *positive thoughts!

Hey Rachel, One side note is that Landlord's choice varies a lot but I'd take a look at local listings that do have a professional property manager and review their screening criteria.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Real estate professional status, as well as the short term rental loophole are a few big ones.

By way of example, I've expereinced instances where the design professional submits drawings and once approved by the municipality, a contractor must associate with the permit, in other instances the contractor must be listed on the orignial submission and in other cases the contractor is the one responsible for submiting the permit set and permit application.

In order to make sure you're optimizing your tax advantages and adhering to all applicable requirements, even while I can offer broad advise, I suggest speaking with a tax professional or accountant who is knowledgeable with real estate taxation.

Not if that neighborhood booms and price per SF doubles...then who cares?

I want to teach students how to House hack to flip/Rent when they are Juniors, Partner them with Professionals Senior year, and then mentor them through a house hack post H.S.  

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

“If an individual is part of a high-deductible health care plan, making a contribution into their health savings account would also reduce taxable income.”Donation to a Qualified Charitable OrganizationCharitably inclined individuals might consider donating cash or appreciated property to a qualified charitable organization, potentially providing a tax deduction to help offset that tax year’s taxable income.