Textbook answer is it should be valued as other buyers in the market would evaluate it. 

Calculators and estimators are OK for general market research, but I would evaluate the home based to comparable rentals on the market.

You need to learn how to evaluate properties for cash flow, not just affordability. 

Would love to see updates on your progress!

I'll update the BP community on my decision and progress, soon. 

Quote from @Edwin De leon: ( Note: Using Va Home Loan to buy Multifamily and will live in 1 apartment for 1st year ) My Goal: With this 1st Multifamily ... goal is cash flow and appreciation 1) Considering Orlando area, but What areas of Florida should I consider buying my 1st 3-4 family house and why2) If you were in my shoes as a 1st time multifamily investor what steps would you take to minimize costly mistake & maximize investment 3) what book do you Recommend to read as a 1st time Multifamily Investor  When considering buying a house hack, you need to first evaluate what your personal goals are.

Clear goals give you a yardstick by which you can evaluate decisions.

This is an important question based on the premise that interest rates are pretty universal.lets evaluate your portfolio for a moment and see if this is really true.Are you looking to refinance one property, or a portfolio of a few properties?

When you have enough saved that losing $25K will not be catastrophic and you have enough knowledge to evaluate the risks associated with a syndications, join a syndication that you have establish a relationship (so accredited investor or sophisticated investor is not required).  

Ive doubled down on myself and decided it can be tough but some things i try self evaluate daily are; "am I educating my self?