House hacking is a great place to start you portfolio, just be buckled up for the long haul.

If it’s feasible, how long might the process take, and what costs could I expect for the necessary permits?

I am not familiar with that market but if as long as the numbers, property and tenants make sense, you'll be doing well.

Some other factors to consider - How long are you planning to hold this property?

Prior  successful flips or holds3.

Working on my own mindset shifts from viewing success as a final destination but more as levels with it’s own set of new challenges and objectives.

I own 2 properties successfully and looking to acquire more to build my financial portfolio and to provide quality homes for those in need. 

"Safely" being taking deprecation on other long term capital assets 

Anyone that is "that successful" either doesn't need to the money, so wouldn't be raising a fund, or isn't that successful, so presumably is using investor money to fund the lifestyle.But at the end of the day, I am more in the camp of Chris: if it is too good to be true, it is almost certainly not true.

The exception is a reverse mortgage which have breach terms that include death of last debtor on title or a surviving spouse.From a practical standpoint, mortgage lenders and their loan servicers are not looking for a reason to accelerate (call loan all due) but may be triggered by poor admin practices of sub-2 buyer.