If it's a lender that does not allow me to speak to an underwriter, see guidelines, or speak to an account manager, I will try not to work with them, unless I know the Account Executive is very experienced. 

You need a reserve to handle unexpected costs, particularly during the first 1-2 years of ownership and learning how to manage the property. 

If part of the property is rentable while renovations are happening, that could help offset carrying costs.Given your construction background, you’ve got a huge advantage in managing the project efficiently—it’s just about getting through the red tape and de-risking the unknowns before pulling the trigger.Have you talked to any local investors or contractors who’ve tackled similar projects in Wicker Park?

I own a property management company and also a contracting company in Ventura.   

However, I’m actively managing my investment, taking on risk, and improving the property, which has significantly increased its value.

I’ve been in the STR game for 6 years, managing multiple properties, and here are some of the tech tools that have been game-changers for me—both for evaluating and managing properties.   

I live in California (Central Coast) and have built a 12-door portfolio in Detroit, which has been a great market for both cash flow and long-term potential.Detroit still offers properties well below the $150k mark, with strong rent-to-price ratios and a market that’s seeing growth in key areas.

They’re ideal for those building portfolios, as they don’t require extensive personal financial documentation.A key tip is to ensure the property’s cash flow comfortably exceeds the lender’s DSCR requirement (typically 1.25x or higher).

I have used TurboTax and Taxcut, so I am looking for an accounting/property management software for Mac.Thanks in advance.

We have two properties in SLC area and manage from out of state.