What can I expect for timeline, potential issues, rough costs? 

Quote from @Leah Miller: @Justin LandesmanInsurance has been bound for weeks already so that shouldn't be an issue. 

However, anything that impacts functionality like plumbing, HVAC, or safety issues should be handled before listing to avoid turning off potential renters/buyers.If you’re re planning to lease it, tenants will expect everything to be move-in ready before signing.

The issue is his definition of cash flow. 

For example, ask about typical costs for HVAC repairs, plumbing issues, or roof work.- Use Historical Data: If the seller has accurate financials, their expense data can be invaluable.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

Meanwhile, the sellers who are most likely to offer creative financing are normally the owners of  real estate that have issues.....condition.....low barrier/over supply market......or perhaps pricing issue, and one of these factors is why its not marketable in a arms length transaction and why creative financing would be accepted.

Covering the mortgage isn’t an issue, but I’m considering factors like: Multi-Family: House hacking would help offset costs right away, but I’d likely need to put money into renovations upfront.Single-Family: Easier move-in with no immediate renovations needed, plus potentially lower tenant turnover once I rent it out For those who have been in a similar situation, what did you choose and why?

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

First off, pardon me if I misunderstand things given the limited amount of information I have, but there are 2 things right off the bat just from your description that could be contributing to your issue: 1) a 2nd floor unit - I had a similar setup for a duplex I owned in St.