I live in one and rent the other for positive cash flow of $400.After all is done, I would have 2 rental properties.

Income is $600,000 per year and husband and wife both work full-time non real estate jobs.
Is it true that the tax benefits are greater, or realized more quickly, on purchases like furniture or televisions to itemize...

Those are even-sized units so equal on rents in theory.

Charging a live-in aide rent.13. 

I've already invested in a duplex in NJ (I'm renting it to two families and managing it) and a single family in MI (living in it).

I plan on renting this as a Long Term Rental and market rents are 2200 in that area.

It is unlikely that they will get rid of the dog if they stay, And you may be looking at boot out situation with legal fees and added time collecting no rent compared to just letting them out of the lease.

The goal is to eventually rent out the entire house, pull equity out of the first house, and repeat the process.

She's been renting it for $2,800/month and the condo has a $600 monthly HOA.I want to offer her $350,000 for the condo (its a fair price for it), 5% down payment ($17,500) and pay her monthly $2,000 for 3 years, after which I would refinance and pay her out.

I've been renting out my 3/3 end unit townhouse for the past three months through Furnished Finder, to a great tenant on a four month lease.