The struggle comes when you plan to sell, pay close attention to how the bank would treat the loan in the event you would sell.Even though its a bit more work, banks are typically open to these loans as it provides them with additional collateral in the event of default.  

Cash for keys is probably not effective since they don't have anywhere to go [most LL are not likely to rent to them] however, I plan to have that conversation and offer any assistance with moving.Thanks again

And don’t underestimate the power of direct outreach; some sellers may be more flexible if you present a clear, structured plan for partnership or financing.

If I have several options, I would prefer a HELOC with no initial draw requirements (i.e. to establish a literal line of credit that I have no specific short term plans to use), i.e. not something like the better.com HELOC. 

If purchasing new real estate as part of your reinvestment, a cost segregation study can maximize depreciation deductions, offsetting future taxable income.For effective planning, assess how the sale price is allocated between real estate, tangible assets, and goodwill, as this determines the tax treatment.

I mean I think about it a lot now that we are closing in on 70.. but hey 70 is the new 50 :) And different cultures handle this far differently than others.. this is why you see some new builds catering to multi generational floor plans..

@Marcos Carbi  If you want to allow a payment plan, Tell them this is the best I can do:Pay $xxx cash by tonight at 8pm for November's rent. and then beginning Monday Jan 20, pay $450 each Monday (in cash?

Would you help is wedding coordinating/planning or just rent the space out?

They could give you a more precise estimate and help navigate zoning regulations and permitting.Let me know if I can help or if you want to discuss your plans further.Best of luck with the project!

I spend a total of 5 days a month performing maintenance related duties(replace flooring, windows, plumbing issues, ect.).