A cash-out refinance or home equity line of credit (HELOC) can be powerful tools to keep your momentum going.Focus on Stability:Look for investments in areas with strong job markets, population growth, and consistent rental demand.

-Looking at landlord-friendly states with strong rental demand.

This can provide a better depreciation benefit than traditional STR real estate.If permanently affixed to land, it qualifies for real estate depreciation (27.5 years for residential properties).Considerations:Zoning laws and campground restrictions may impact legality.Self-employment tax risk arises if you provide substantial guest services.Vacation home rules apply if personal use exceeds 14 days or 10% of rental days, limiting deductions.Audit risk is high, so keep detailed records of participation, expenses, and rental operations.Given the potential tax benefits and complexities, consulting a real estate tax professional is advised to ensure compliance and maximize deductions.This post does not create a CPA-Client relationship.

The only thing that I receive are monthly invoices with fees that they cannot substantiate.

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

Trying to find out if there just isn’t the demand, or so much demand that the available units are rented so they don’t show up.

The location hasn't had a lot of demand which has made it challenging for him to find an end buyer. 

I find that internet providers, like Comcast, tend to update their technology and offerings to better speeds as customers have higher usage demands.

Both properties have a substantial amount of equity that’s essentially sitting idle.Would it be a good idea to tap into this equity (through a HELOC, cash-out refinance, etc.) to fund future fix-and-flip projects or purchase additional rental properties?

As a result, the few homes on the market command higher prices due to basic supply and demand dynamics.Many homeowners hesitate to sell despite potential profits, as replacing their home would be significantly more expensive.