Purchase price: $8,000 Cash invested: $20,000 In 2013, I decided to put much of what I had learned from books into action by purchasing a two-bedroom home—not as a traditional investment property, but as a home for my mother.

Just a follow up question, were you utilizing debt to invest, I have always been taught since a young age to try and not utilize debt (I come from a family of stock market investors, traditional business owners) where debt is not utilized as frequently which I obviously understand debt can be a very powerful tool and utilized in a great way its just something I want to avoid with my investments to an extent any suggestions for investing without debt or as little as possible. 

If it’s a structured settlement and you aren’t getting a lump lum, you could contribute some of that to a Roth or Traditional IRA each year, or if you are self employed even more to a SEP IRA.Also what’s your short term, mid term and long term objectives?

You will owe monthly payments until you fix the property up, rent it out, and refinance to a more traditional 30 year fixed rate product. 

Is STRs the way to go in Hawaii or maybe just traditional LTRs instead? 

When you do a traditional 1031 exchange you have 45 day identification period, to provide a list of potential replacement properties and 180 days to close on a replacement.

Can they be listed alongside other traditional MLS listings?

FHA is for sure not going to be an option for him, last option is purchasing from an investor with owner financing, or lease to own program where he will not need traditional financing. 

Honestly, I've given up on finding cashflow anywhere close to the city due to rates and prices, BUT some other opportunities you may want to consider are:Live in flip - mentioned earlier in this thread, always a solid option in any market.Condo conversions - good money to be made from this and since they're a little trickier than a traditional flip there tends to be more inventory available that would allow for a profit.ADUs - come February 2nd, ADUs are allowed BY RIGHT on any SF property in the state, owner occupied or not.

While traditional loans might be tough with current interest rates and no W2s, there are definitely creative financing options and strategies to consider.One possibility is exploring seller financing.