I figured now's probably the best time to take some risks given that I'm financially stable and have build up a good amount of savings.

My goal is to have enough cash flow from my real estate investing to become financial free in the next 10 years.

If you are going to invest, you'll get back more than your financial investment on your first transaction and you'll learn a great deal.

I'm unable to come to a conclusion on whether it would be more financially advantageous to keep what's there since it's not broken and increase the rents accordingly rather than add on such a project.

When you have a seller that looks at 10 offers, the only real value that stands out in an offer is WHO is presenting it.

I was thinking about putting in the following:Personal financial statementPrior rent rolls on the property for 3 yearsSome type of public report on the value of the complex (zillow or other) ... not sure on this oneA profitability statement ... thinking about using the one on this site from https://www.biggerpockets.com/real-estate-investme...

Extremely likely it would require a personal guarantee, so the lender will look at your financials.

Since its our neighborhood and a smaller number of properties, we want our letters to stand out and be personal, yet also want to protect our family's privacy - we have two small children.

This helps because If you own that entity that stands in as Trustee, you'll have total control of the property because you own the entity that's Trustee of the Land Trust.Hopefully, this helps and you're able to use this for many transactions to come.      

Since they're not the best tenants, and you'd rather have them gone now, you could offer to let them out altogether and start over if you're ready; otherwise, I don't see how it benefits you to now only have one person financially liable instead of two.