I've encountered several situations where tenants not only broke their lease but also caused damages, sometimes even leaving before the lease ended with damages behind.To clarify, when I mention damages, I'm not talking about normal wear and tear but rather significant repairs costing between $5,000 to $8,000, which don't qualify as vandalism for insurance purposes.In the past, property managers I've spoken to have often discouraged pursuing tenants for these damages, citing it as not worth the effort.Here are my questions for you:- Would you pursue the tenant?

I also included a financial stake int he end deal if I closed.

Find someone in your local market who moves a ton, go 50/50% with him or her on your next deal and let them manage the sticky situations and get through the barriers.  

It's always a challenge increasing rent in that situation.

Whether dimensions or financial data.

Here's my situation in short details:Bought a commercial property for $699K in 2019 through a 1031 exchange which cash flowed beautifully until late 2022 when the tenant bankrupted and moved out. 

What's a better situation for seller financing? 

It may be worth speaking with a different lawyer or financial advisor to get a second opinion and weigh the pros and cons of each option before making a decision.

If you can take a little financial pain, I think it is better to list in the slow season.  

@Phil AveryConsidering your financial situation and the current market conditions, each of the options you're contemplating has its own merits.Given your inclination to begin with a significant amount of equity, option 1 may be a good fit for your objectives.