Cash is better of course, and any other red flags with their history would make the cashiers check more suspicious.

You'd evaluate comps, speak with realtors, and document your findings.

Hi Everyone, I am negotiating a property in Florida with a motivated seller and I noticed that in the sales history of that property there are no warranty deeds.

And the documents have to be notarized prior to filing. 

You may be confusing documents and patterns.An affidavit death of joint tenant would be recorded along with a death certificate but would not necessitate a probate to effect an insurable transfer.There are summary probates in some state that require minimum court involvement.In my state, CA, a formal probate is required when the Decedent's interest and their total gross estate exceed $150,000.

Here is a link that explains it.https://www.michigan.gov/documents/2856_11014_7.pdf

Some lenders require a 2 year history of managing rental properties before considering the rental income FYI.  

Any turnkey provider can fix a house and sell it "turnkey" but the less reliable companies will never manage their own tenants or their own repair work.Similarly, property management companies that know both (1) the condition and history of the property, and (2) know the tenant is the best type available, will have the best return on time and money.We can PM if you'd like further details, I don't intend to hijack the thread :)

How do you guys analyze an applicant's rental history?

They basically just send you some documents with different rate options (ie: 6 month open mortgage, 2 year term, 4 year, 5 year, and rarely a 7 or 10 year option).