One of the institutes I receive monthly updates looks very closly into housing debt and credit, HELOC utilization, equity, lending standards etc - with 2008 as the bench mark, all indicators are deep green.I am however concerned about goverment debt and the 6 trillion dollars we have "printed" - this may not go without consequences, probably increased inflation, which hurts anyone with savings and benefits anyone with cashflowing mortgage debt.

However, there are some smaller institutions and and portfolio lenders that service their own loans that will forgo that seasoning period.

I own a rental where flood insurance through the NFIP was a deal breaker, and I was about to go the elevation certificate route (I think the estimates I got for that were ~$500) when I discovered that I could get insured through a private company at a fraction of the cost, and the lender was fine with it.

If so are there any specific lenders/institutions or programs any one has experiences with?

The plumber was great, did excellent work, but was real expensive.We paid for most of the materials on credit cards (Home Depot, Lowes, Visas, Discover) and took a loan out on our Discover card to pay for everything else plus cash from jobs.

I have no investments currently, but I hope to change that within the next 12 months.I got turned on to real estate investing through a random youtube video, which led to discovering Bigger Pockets and a slew of other podcasts and video series, which in turn led me to a load of books on the subjects that I've been practically drowning in for the past couple months. 

As we discovered with the listing in Oxford  - there is a reason it sits, but sometimes it may just be an easy opportunity. 848 Piper Road Ashby, MA was such an opportunity, tough project to be sure but we made a good profit. 

I've had a policy cancelled before because a tenant got a pitbull unbeknownst to me, discovered during an insurance auditors drive by. 

Or perhaps other options you have discovered to be more effective in finding a entry point into the local markets?  

Following the guidelines, you cannot have more than 10 “Financed” properties.However, with COVID, I’ve seen more lenders institute a max of 4 financed property overlay.