Even if the rental has a decent cash flow with additional flood insurance, we're still not sure we want to take on that risk as we are out-of-state investors (planning to move back to KY in the future, but not now) and we don't like that it will potentially bring down the perceived value when we try to sell it in the future.The seller has never lived there and has not provided any information on if it has flooded before or not. 

My plan is to add 2 - 6 shipping container type of small houses and an above ground pool at some point to make at least a section of the property short/mid term rentals.

Quote from @Daniel Tanasa: Another option is to get a small cash out refinance from the house you plan on fixing up, if is in financeable condition, and use that to fix it up, while still cash flowing.

My plan is to start house hacking.

Many people choose NOT to have this, because the administrator will then vet every investment you make to ensure you do not invalidate your IRA.Invalidating your IRA means that you've done a prohibited transaction and the entire account is then deemed as distributed to you.If you don't want checkbook control, then I recommend a plan administrator such as Equity Trust - www.trustetc.comIf you are sure that you're aware of all the rules around prohibited transactions and disqualified people (who you can and can't do business with), then a plan administrator like Sense Financial would be a good place to start talking.  

Unfortunately, while there are other methods to acquire investment properties, the reality is you need cash and reserves to plan and set up your investment portfolio accordingly. 

@Chris HainsI use the House Flipping Spreadsheet (https://www.houseflippingspreadsheet.com/) to do the planning, analysis and estimating prior to purchase. 

.🚨 Common issues I see:❌ Not properly tracking repairs vs. capital improvements❌ Missing out on cost segregation & depreciation write-offs❌ Scrambling at tax time instead of planning proactivelyI’d love to hear from the group—what’s been your biggest tax headache as an investor?

As important a consideration is how will you reinvest/spend the proceeds from the sale to build wealth.Hope this helps.

Yes we definitely encourage everyone to STICK TO THE PLAN when renovating!