(Even discussing a home for sale that you don't already own is a license-required activity in MA)Remember that we operate on 100% commission. 

And remember that you will be signing a personal guarantee with any commercial loan.

I have not done this personally but I remember hearing on a BP podcast with @Brie Schmidt that she has purchased multiple homes on a portfolio loan.  

My ideal retirement still involves working in real estate, it just means I’m not working my 9-5 and I can take a 6 month+ vacation away without having to worry.

Ideally I'd want something near my place of work I can house hack.

Actually, here is my "starting up" collection:Read http://greeneincome.com/index.php/2018/10/29/ideal-vs-desperate-investor/Read Dave Ramsey book "The Total Money Makeover: Classic Edition: A Proven Plan for Financial Fitness." and complete the baby steps there.Read Scott Trench’s book “Set for Life.”Finish the school and get your degree - you'll need it later, especially if it's business management.Get a job first where you have W2 income.

You have to remember, these banks are investing in you as well as the properties, so try walking into a bank or two or ten with a list of your holdings and show them why their investment would be safe with you.Hope this helps,Bruce

I ideally want to start with wholesaling because of the little capital I have to my name and I can learn a lot about real estate.

Remember, our main goal is to get this under contract so we can make other buying and business decisions.1) We'll give him an 11% earnest money deposit.

this is fairly common practice in low income areas Ideally you’d never do this but in some rough neighborhoods where everyone is on assistance it sure can help