For me, the reports available in Baselane are ideal, but I'm also not trying to run a different business through it like it sounds like you may be doing.

An accountant is a general job title that may potentially do one of many different tasks(bookkeeping, reviewing financials, assurance, taxation, etc)Bookkeepers are specific that they will likely only do the bookkeeping.

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

When an investor gets over 4-5 in a market then we normally talk about diversifying into a different market. 

Hey @Michelle Baldwin, yes this is a challenge but everyone said it best.Simply, you can just use a different browser to be logged into each VRBO account.I also think that @John Underwoods idea will work as well.

Quote from @Tom Server: I beg to differ @Nathan Gesner, about the financially disciplined.

Not sure why the process would be any difference for a voucher holder in a duplex or single family.

Because when a hot deal comes up and you need to close fast, that relationship can be the difference in scoring the deal. 

My CPA was unsure... do you issue 1090-NEC for the difference between 1099-K and 1099-MISC or do you double up the income (i.e. 1099-NEC for gross rents from PM, 1099-K of the net owner distribution on 1099-K, then owner reports double income and puts a line item expense for the 1099-K since 1099-MISC covers gross rents).You need a new accountant lolPM issues 1099-MISC, not NEC for rental income paid to property owners.You would still issue the rental income paid to the owners regardless of the payment method.The Property Owners should add an expense line item on Schedule C stating that income reported twice on Form 1099 to offset any duplicated amount.

I realize that everyone will run a MTR business differently and I prefer to learn from different operators and develop my own technique