@Rochelle GerberHere are some of the downsides of putting real estate into an IRA or 401k.No tax deductions: You can’t claim deductions for property taxes, mortgage interest, depreciation, repairs, improvements and other property-related expenses.Property expenses: All expenses, repairs, and maintenance costs must be paid with IRA or 401k funds, and you must pay others to do repairs and manage the property.

Make sure both properties have all the repairs and maintenance needed and no major cap ex is needed before you try to add one on double leverage.

Because of this, I'm exploring what it would look like to begin investing in vacation rental real estate as a way to:1 - Save on taxes by taking depreciation2 - Hold long-term appreciating assets3 - Have properties where we enjoy vacationing that we can stay at when we go to do maintenance (probably 2 areas).What resources would you recommend for someone just starting out who has these specific goals?

The highest quote I got for my duplex was $2600 annually and the lowest was $1300.

Here's some other copy & paste advice you might find useful:---------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

You will always have taxes and insurance and maintenance and capex anyway, so how much better will you sleep because you eliminated one of those expenses?

--> $50K minimum investment, with at $10K SWAN account to cover expenses related to the purchase of ONE property, including ongoing maintenance while the property is rented for a 4-5 year term. 

It's free, handles rent payments/reminders/late fees, maintenance requests, some reporting (e.g., P&L), tracking expenses and income, rental listings, lease signing, etc. 

Less cleaning but maybe more maintenance.

Invest the $550,000 in a mutual fund such as S&P 500 or VTSAX with a 10-year history average annual return of 12% 2.