Primarily rented to military- never had a problem, required to end lease or evict. 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases.

As for the leases, would you recommend keeping the tenants, potentially raising rent, and extending the lease to a long-term rental, or would you recommend finding a new tenant? 

Great thanks @Michael Smythe, in your experience can you itemize the tenants that have the Resident Benefit Package? 

You'll need at least a 20% DP to purchase the next primary, and probably a signed lease proving rental income.

I will use the rent by room strategy for a year, then move out and lease the condo under 1 lease.Does anyone have any advice about condo hacking, or can anyone describe their personal experience?

It's great to ask these questions in the forums to get a feel for things but it's not a substitute for getting "official" advice from an REI-savvy tax pro that you have hired.Regarding what to deduct versus what to capitalize (and depreciate over time), your tax pro can walk you through that for each line item.

It requires a lot more work, follow up, and it's necessary to have systems in place to support the tenant vetting, rent collection and creating lease agreements.

There really aren't any agents that do just leasing for people of residential homes 

For investors who own or have owned wedding or event venues, what are the typical lease terms you've leveraged?