I originally didn’t lay blame, or pursue damages from this tenant to reimburse my insurance deductible, but his behavior now is making me regret that.

As promised I'll go into behavioral economics to assist you further in a different post because this one is already way too long.

Making 3 columnsColumn 1, selling traditionally with an agentcolumn 2, renting it out with a property managercolumn 3, seller financing in FloridaColumn one a go through all the cost to sell with an agentand also go through the time it takes to sell with an agentdays in the market (DOM) tell the average amount of time it takes to sell a house with an agentSo it's costs money and it costs timeColumn 2, renting it out with a property manager, there are risks and rewardsA property manager cannot guarantee cash flow so you can make your bank paymentA property manager cannot guarantee will be no damagein a property manager does not keep an eye on the property that much, maybe once in a whileso if there's an eviction you have to pay for itand if this damage you pay for itif there's no rent coming in, you have to pay the mortgageColumn 3, I generally talk about seller financing in generalthere's lease to own and owner financingLease to own you turn the property into an investment propertyyou are landlord and you have to pay the mortgageyour to pay maintenance and taxes and insurancehopefully the behavior of your tenant buyer versus a regular tenant is better, money on time, no damagethe tenant buyer wants to buy the propertythe tenant buyer does not cause you trouble as the landlordthe buyer wants you the landlord to give them a good recommendation when they try to get the mortgage down the road; they need their landlord to give them verification of rents (VOR)Owner financing means you're selling the property and the owners have a deedit's a little bit like contract for deed where you pay on a contract, and you can either finish the contract or refinance contract and pay off the existing financingHow to sell subject toit's important that you read this next sentence,I DONT BUY SUB2 UNLESS ITS A PERFECT HOUSEwhat's a perfect house?

Or more specifically:1 - is this behavior a truthful action in lending?

No one has as robust of MFD ( multi function display) as tesla.. its just wicked smart. 

Hopefully, he will change.If his behavior continues, write a letter communicating the same.

Cap rate is a market-driven metric, which measure the attitude and behavior of all market participants.Here is a BP link I think will help you better understand:https://www.biggerpockets.com/renewsblog/2016/05/31/cap-rate-formula-include-debt-service/

I just finished my Doctorate (I'm 26) and am working as a nurse practitioner and quickly realizing that if I make this my entire life I'll end up on the other side of the locked psych unit (I work in behavioral health).

I fell into this behavior with my very first rental property where my tenant took advantage of my kindness and 2 days late on the rent turned into 2 months behind in the rent and I ended up having to evict the tenant.

If this is repeated behavior or you have caught them in a lie that is a different story.