Question: If we purchase a new primary residence and convert current primary into rental, then would we (married couple filing jointly), be able to sell BOTH homes capital gains tax free on up to $500,000 profit each? 

I'm trying to get myself set up with some analysis tools for MF investments, and I really like the "Value Play" model that Berges has in his "Complete Guide to Buying and Selling Apartments".

I can listen to books and educate myself on whatever I want while at the gym, in the car, etc.I currently have 200+ books in my library and if you'd like any recommendations on a particular area of study, send me a message and I'd be happy to provide you with some.A couple I'd recommend that will give you a "crash course" are..Buy, Rehab, Rent, Refinance, Repeat - The BRRRR Rental Property Investment Strategy Made SimpleFLIP - How to Find, Fix, and Sell Houses for ProfitThe Book on Flipping Houses How to Buy, Rehab, and Resell Residential PropertiesThis book is not currently available on Audible but a must readThe Book on Estimating Rehab Costs - J ScottBigger Pockets has become one of my best resources.

having started my Career selling lots and land and buying them at tax sale.

Is there any other way around waiting a year to sell?

Here are the details:Bought in 2015Owes - $45kNeeds additional $20-25k as a down payment on the new house for equity.Rate - 6.125% (Adjustable Rate Mortgage) Max is 8%PITI - roughly $700/monthHouse is in great condition so no rehabAsking $175,000, could sell on market for $220-230kRents - $1400-1600How would one structure this deal?

Second property purchase price was 275k (so added some other funds to make up the total figure), and potentially looking to sell around 315k.

That's great on paper and makes you happy with yourself, but when it comes time to sell small multifamily you're not going to force a double in sales price by doubling the NOI. 

The goal is not to be constantly trying to sell to them, just provide them value and get them interested in wanting to come back to the area, new things at your properties, calendar of events for the area, etxc 

3) the back of the property leads to a cul de sac which could potentially be another entrance - option would possibly be building a duplex or fourplex which would be less costly - then sell it and make another and use the profit towards the apartment building and just build 1 because who has that kind of money.