These two achievements will definitely help you in securing funding for future projects, as private lenders consider experience when deciding what leverage they're willing to offer you.

I earn around $15k/month from my business, but my income is somewhat variable, which might make securing financing challenging.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

I priced it only about 14% higher than the long term rental which matches traveling health professionals' budget on Furnished Finder.So I'm leaning toward longer term rental because even if I secure midterm tenant, that 14% more isn't really worth the potential vacancy. 

Security Deposits:The property management charges tenants a "move-in" fee rather than a security deposit.

DSCR loans don't require personal income verification or a debt-to-income ratio, making them ideal for properties with strong cash flow, even if the current owner has credit issues.Here's how it could work:You could use a DSCR loan to refinance the hard money loan, securing more favorable terms without having to involve the seller's credit.Since the rental income easily covers the property’s debt service, you’ll be in a good position for lender approval, bypassing the conventional mortgage route.This approach could allow the owner to stay in the house, while you take over financing with a less restrictive structure.

If you’re looking to build REAL wealth, then leverage of one type or another is necessary.Debt is one type of leverageSyndicators leverage investors capital as equityStart up companies leverage Venture Capitalists investments in both equity and debt.The real estate investor has 3 distinct “cycles” with debt leverage1st stage is debt secured by real estate but also personally guaranteed and often cross collaterialized2nd stage is debt secured by real estate but liability not personally guaranteed and recourse limited to specific property.3rd stage is debt free If you own units in a syndicated real property investment and the investment is leverage by debt you may not think of it as YOUR debt because you’re a passive investor, but your investment is encumbered by debt the same as property you own individually IF you haven’t personally guaranteed the debt.  

But you really only get 1 or 2 questions max and how is that really gonna help you secure a deal?  

There isn’t a perfect science, really it depends on what will make you feel secure.

Here are the Positives:Upfront Payment: The tenant’s offer to pay the full year of rent upfront, along with the deposit, shows a commitment and provides financial security for you in the immediate future.At least She was Honest in Her Communication: The tenant has been transparent about her situation, which can be a positive sign of reliability and sincerity.My Negative Concerns:Her Future Financial Stability: It's only a one-year lease, if her medical condition and financial condition should worsen (Heaven forbid), you may have to face her wanting out of the lease earlier than the 12 months and eventually you may be faced with having to decide not to renew the lease (after her 1 year contract is expired) based upon the sad news of her condition becoming worse, (Heaven forbid).