Very fair questions raised here.

And a property manager is expensive and profit margins on rentals are fairly small.

That said, expect to deal with a fair amount of fluff leads.The two best strategies I’ve found are inbound methods: direct mail and Google Ads.Direct mail can be expensive, but it can also yield highly discounted properties.Google Ads, on the other hand, doesn’t require data extraction like calls, direct mail, or texting.

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).  

I am worried though if we break from Evolve, the upfront stuff might suffer and communication with guests.  

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

What if a property is slightly rundown and would need to have some renovations done before it could rent out for fair market value, would a DSCR loan still work for that? 

Some are responsive, fair to LLs and easy to work with -- others are slow, difficult and maddening difficult to work with.  

You need to look at the credentials of the person offering the education and whether it is him offering the education or just one of his assistants.The cost should also be reasonable, in my opinion.If you are taking a class, not a personal 1v1, I don't understand why a class would cost more than $100 an hour.If you are getting 1vs1 communication, I can then see it costing $300+if the person does not have an visable experience, I would not consider paying for the experience.I also question these investors being oversold on someone they don't need.In my opinion, a person can retire by getting 10 homes backed by fannie mae / freddie mac loans.The oversell to getting outside capital to get a large complex is likely being sold to investors who don't have / make a lot of money.

I bet the numbers look a fair bit better than here, I would hope.