I'm 30 with a family of four, just bought my first primary home this year.

No rental signs, minimum 1-2 year owner occupancy, restrictions on the number of rentals, etc. 

@Vernon Welch II most tenants offering to pay their rent upfront are trying to compensate for negative qualification issues.NEVER override your screening process just because someone offers to pay several months upfront!

It seems like it basically up to you to do the math on how much more you will potentially make selling each unit individually and then deciding if that extra $$$ is worth the number of extra hours you will spend.

Cost to build- which should be double now, if this property is more than 5 years old., B.  

Cody,If you want to work with a bank or lender to build on a piece of vacant land you will need to be on title of the land for at least 6 months.

I will spend around $5000 - $7000 a year for tax planning and filing.

@Jon Fletcher There are basically two potential options. 1) Amend the tax return in the year of purchase and prove you used capital gains to purchase the property and 2) Sell the property to an OZF, follow the 20% related party rule and then the structure of the sale of the property to be able to reinvest the gains.

I was helping other invest in these types of deals and wanted to buy one for myself.

It's great that you are getting ready to take the first step to house/room hacking.