I'm curious how many hosts update their listings depending on the season.

This all comes down to how you're structured, how the flip cost were accounted for, if there is a partner (you mentioned "we").If it is an S Corporation and you "distribute" or "sell" the property to yourself, if there is any loss on value, which probably there isn't, know it most likely won't be deductible if it's a related party transaction.  

Curious on your thoughts.

Any thoughts on Bloomfield, NJ or other towns that could appreciate well and have or lead to positive cash flow? 

Savan cool well it is good to start and when it is the first deal it is wiser to be cautious and not over extend one self on the payment and rehab costs.

I'm not sure what you'd learn that you can't find online.

The only reason to get your license in your context would be to get access to view vacant investment properties for yourself on your own schedule and for access to the MLS.

That is what I did here when I started investing in 2020.Here is an article with more information on what a house hack is www.rocketmortgage.com/learn/house-hacking

My water usage bill is the same,  general lability coverage is the same, if and when I have to replace my water service line it will cost the same, the cost for my lawncare and snow removal costs the same, exterminating services cost the same and the list goes on.   

It is also a higher quality contact because you can confirm if you're actually reaching the owner.Mailers take up less of your time (aside from ordering and distributing), cost more, and are more challenging to track.I'd start with calling then add on mailers.Best times may vary but we find that we get the most people on the phone 8am-noon and 3-7pm.