If we combine these separate lots  back into one big property, is there a way to do it, so that it's seen as 5-year seasoning?

If they combine the final sale with a seller carry back note, they can spread the tax over a period of time. 

Anything in real estate so much depends on the location, the type assets, surrounding amenities and what you expect it to do for you.I use Lockstate remote WiFi locks because they are currently the best and solve all the problems a modern smart-lock needs to accomplish: getting the right people through the door at the right times without me having to be there.I run and experiment with various Airbnb solutions:Manage villas for clients in TuscanyHost a turn of the century restored 6 room apartment in a quaint German city near the beach.Manage varying types of other apartments, condos, and houses in various locations in the USA and Europe.Keep in mind when dreaming of the "big bucks", it takes time to:Set up and maintain your Airbnb and various other accounts.Set up each new listing.Communicate with nice and not so nice guests.Factor in vacancies and damages.Outsource and manage cleaning and fixing team.Your dwelling needs to make at least the same income compared to the long-term rental if you're only looking to grow equity.

Combining wholesaling with back taxes and owner financing would be a challenge even for a veteran investor.

The mortgage, taxes and insurance are combined in escrow.

I like buying them at 90-95% face value and combining that with other discounts

As others have mentioned, state and local laws, in combination with the terms of the existing lease, will determine the necessary notice period and whether there is a limit on your rent increase. 

I use a combination of Zillow, Redfin, and FindCompsNow and I find them to be missing a small peices of data some times.  

AllWe have a contract on our first home to start flipping, (exciting) from asking around we have received different answers to our question, "what insurance should we carry for flipping homes".We have received the following, Builders Risk, Liability, Home owners and few others, should we carry one, all or a combination.

The entitlements, however, may cost 10s of thousands.Once there's interest, things can be adapted to fit whatever tenants want, for instance combining two pads with 2000sf restaurants into one pad for a 4500sf restaurant.