I must say you are taking the right steps at becoming more educated on investing in real estate.There's lot of useful and strategic planning tips on the forums and site. 

They would say that what you're really looking for is an investment loan and an owner-occupied loan is not something they can approve you on.So, if you plan on using the house hacking strategy multiple times, you should be as strategic as possible with selecting the size, location, and the unit in which you will be living in the properties you buy.

I thought moving to Orlando, a growth market, was the smart strategic move.

I'm nervous about tying up $50K by buying and holding the lot if I cannot build soon since it would mean delaying other strategic priorities.I'm finding that most banks won't do individual construction loans for investors. 

@Cathy Li Being from a city or having family that lives in a city is not a strategic reason for choosing a market.

I would say put as little down as you can (you may be OK with 3% or 5%), as long as it's still cash flow positive and your net operating income is at least 20% over your mortgage payment (principal and interest), which is also called having a debt service coverage ratio (DSCR) >= 1.2If you do that you may have more available for a down payment on a fourplex, which you also may not need 20% down for.If you still find that you don't have enough for the down payment on the fourplex, you could try strategically improving the duplex to try to increase its value, and then refinance a year or more later (similar to the BRRR strategy).You can also try finding a second property (fourplex/whatever) which has equity and which you could buy with seller financing, where again you may not need as much down or may be able to negotiate creative terms which make it work for you.If prices just don't make sense and you aren't able to buy and have positive cash flow with a DSCR >= 1.2, it may also just be better to wait until the market cools down.

If strategically that gives me an advantage then I am all ears; I am trying to absorb knowledge and not stick to potentially preconceived notions that aren't beneficial to my "business plan". 3: Financing is good for me, but I've never shied away from discussing deals that make sense.

Ideally, you want to find an experienced CPA who works with real estate investors like you, can help you strategize and keep that tax bill low, and who you feel comfortable with and is the best fit for you.Good luck on your search :) 

Thanks in advance to any/all feedback.  I presently own a two family rental in the North burbs of Boston.  I have a little over 100k in equity but the market here has been crazy and I was thinking of selling it to buy...

It also helps to send out a strategic tweet when the communication slows to a drip.As for the information provided on the website; as many have said before DO YOUR OWN RESEARCH.