I've asked my clients a similar question and have developed tools for them to minimize this, but I find there are a few different types of clients.Manager managed - these folks have no issues as they simply upload their year end statement from their property manager, their 1098 mortgage statement and any other one-off expenses they may have paid for outside of the management company. 

Bad tenants and squatters are wholly different situations.

@Dylan Gomez When selling your inherited property, your taxable capital gain will be the difference between the sale price ($380K) and its stepped-up basis (the fair market value at inheritance, likely $250K), minus selling costs (e.g., realtor fees) and documented remodel expenses ($50K).

. - New construction will be comped against other new construction - Start out with enough comps to justify the price point- keep the area tight to consolidate the risk vs building one or two in different parts of the same neighborhood. 

Are dti numbers different with primary vs rental as far as getting a loan?

Commercial financing is 100% different (and easier lol)! 

The marketing copy and photo captions, professional photos, and weekly activity on the OTA listing, makes a big difference in bookings.

How long it takes to be financially ready is different for everyone.

and split the difference?

Of course could be a little different but thats generally how it  all works.