It could save you way more than the cost of an agent. 

Since you’re not paying fair market value for the property, any legitimate claim can, probably successfully, convince a court that the “sale” was a fraudulent transfer.As to what to do, you’re not going to find an answer with which to base a decision on in an online forum.  

Insurance is dicey and it's better for me to spend $100K than saving that by using insurance but risking no renewal...

The purpose of course, is to save for retirement in either a deferred or tax free account. 

If you have an insurance claim with renters in the property and a homeowner policy I would expect the claim to be denied.The benefit of landlord insurance is that it will actually cover you, if you try to rent a house out with a typical homeowner policy you are simply not covered (even though you are paying premiums).Insurance is not where you want to go lowest bidder or look to cut corners - it is there to save your behind in the event of a major incident.

A LOT of distrress is leading to mergers and firings, in just the last few weeks, this happened: (Big credit to @NewsLambert)Lower to acquire Universal Lending retail and wholesale operations (11/1/23)Trustar Mortgage acquired by Archer Mortgage, LLC (11/1/23)People’s Bank of Commerce to exit residential mortgage lending (10/27/23)BMO Bank cutting 228 jobs in Northern California (10/25/23)Homestar Financial to wind down operations (10/25/23)City National Bank layoffs in Los Angeles total 71 (10/23/23)Hometown Lenders layoffs (10/12/23)First Savings Bank to lay off 135 mortgage workers (10/4/23)Wesley Mortgage absorbs competitor Colten Mortgage (10/4/23)Cenlar to lay off 85 in Ewing, NJ (10/2/23)Rithm Capital to acquire Computershare Mortgage Services Inc. (10/2/23)Wells Fargo cut 525 jobs in South Carolina (9/28/23)Better Mortgage lays off additional employees (9/22/23)The Graystone Company has acquired Direct Mortgage (9/13/23)Flyhomes to purchase certain assets of Home Sale Assured (9/13/23)Divvy Homes to cut 95 jobs in San Francisco (9/11/23)Farmers-Merchants Bank to sell three branches to focus on core mortgage business (9/11/23)It goes on…..The mortgage industry is in a starkly deep recession.And RIP refinances, unless you are holding an even higher interest rate loan (like a construction/bridge loan or hard money, or perhaps you just fixed your credit.

Getting started is usually the best thing someone can do because prices can sometimes appreciate faster than people can save.

I found this other group called Certified Tax Coach (https://www.certifiedtaxcoach.com/) that help with tax strategies and tax savings. 

The extra five months of rent income would have covered 50% of the renovation and saved me a lot of time and struggle.

I don't hate my job, it's just too easy for me after doing it for 20 years.I have $50K in savings (separate from 401K / investments) that I could use to start but my wife's motivation is to purchase a house for our family.