With your drive and determination you likely wouldn't throw in the towel even if it got really tough, but why not have the first one be a hit and be smooth and you love it and are excited to do more deals. 

A CPA is very similar, determining whether you need a very complex structure or very simple.For syndications, are you looking for an equity play or an income play?

@JD MartinI know you want a simple answer, but there is none in this case.First, we will need to determine whether this owner financing constitutes a sale.

With this info in hand you can determine if it makes sense to move forward or call it a day.  

@Tina LiaoTenant screening includes a credit check, a background check, income verification, references, and interviews to determine financial responsibility.

On one document I received it states: "The individual (applicant) is mentally competent but due to age or physical infirmity is unable to manage his or her property and affairs effectively and, recognizing this disability, has requested a conservator's appointment"It also states the conservator is: "conservator of all assets of the individual's estate".What I'm wondering is do I need the conservator to also be the co-signer on the lease?

For example, if we know the gross rents, how does the institution estimate operating expenses, vacancy, etc for the purposes of calculating the NOI so that they can determine DSCR?  

I'm guessing you also have checked for the ARV and what houses in the area are selling for to help determine if it's worthwhile.

To properly renew a lease with a tenant, several tasks SHOULD be done:1) Evaluate the property to make sure tenant is taking care of it and you want them to stay.2) Do a market analysis of rental rates.3) Determine target rental increase amount4) We present all this to the tenant, as we assume they're looking at rental rates on Zillow, etc.5) We then ask the tenant what adjustment they think is fair and then negotiate rent amount and lease term (we always try to go for 2 years).6) New lease sent electronically to sign.All of this takes time, hence a Renewal Fee.

That will determine the amount of effort you put into your business structure.