Does anyone have any insight to how insurance premiums compare between a 25 yr FP and a 100 yr FP? 

Any major transaction just prior to a bankruptcy can and probably will be viewed as fraud on the bankruptcy court.

The numbers:Purchase Price: $28,500Equity: $49,000 (No Appaisal) Comparables are 45k and 53kFinanced: $0Improvement Costs: Projected $2,500 on tenant turnoverProperty Taxes: $700Insurance: $900 yrProperty Management: $58.33 monthlyVacancy Rate (7%): $42 monthlyRepairs: $360 yrHOA: $420 yrCAPEX: $144 yrMisc/Legal: $349 yrCash Flow:  $204 monthly Rent: $600Cash-On-Cash ROI: 9%Shoot me a pm or leave a comment if you have any questions or remarks!

They paid $66,500 when they purchased the house a few years prior

All the county has to do is compare the current photograph from a previous one to see the illegal structure.

A few people will get lucky, time the market perfectly and make huge returns compared to the other 90% that get into it that will do worse than the S&P 500.In other ways Real Estate is different though - first "Everyone will always need housing" unlike Bitcoin or Pork Belly Futures. 

You'll have more options if you a trying to BRRRR since that will allow you to create equity and refinance out a private lender quickly.Small multi family: This would open up the doors to house hacking and allow you to get owner occupied financing which will require much less down when compared to a non-owner occupied.

Let's say the repairs + other costs amounts to roughly $10,000, I can sell the property for $40,000 - $45,000 at least, and it's still cheap compared to the others.Of course, I need to do further inspection of the property and properly crunch the numbers.

WIthout prior experience flipping, what are the best ways to estImate and strategize how much rehab wIll cost up front (resources, professIonals, etc?)?

For income property, you can get good comparables based on the rents paid and costs of the property - if the seller is using an agent that agent should be able to provide those.A lot of these costs may depend on your location.