Making the right decision upfront is important to avoid the challenges of switching management or service providers down the line.

I'm concerned that I'd buy a place in the winter, then it would either take a long time to find tenants or I would have to charge significantly less in rent to avoid a long vacancy.

Just fixing a property over 2 years, then selling it and avoiding capital gains tax, then repeating.

Consider off-market sales to avoid public listings and minimize tenant disruption, using discreet marketing or a wholesale strategy.

Once that phase is complete, I’d transition back into long-term holds.As for the cash-out refi, without at least doubling the rent, I’d be in a net-negative position each month, which doesn’t seem like a worthwhile trade-off.On the tenant side, I agree with your point about the business aspect—it’s something I’m working on coming to terms with.

Don't hire an agent if youre trying to avoid agent costs.

To avoid the risk management/insurance that comes with tenants' wood fire use:I'm thinking to seal the chimney cap on roof and run a cord putting an electric Infrared heater fireplace in there, so they can still open the glass and get heat and watch TV over the mantle, but can't burn anything or have any flame.

You might want to limit your visits though to avoid escalation.Short term if the smart lock is on his personal door just change it to a key if it's isn't working for him, you can always switch back later.

Having that strategy in place will help you avoid potential stress when the time comes.Overall, I think this deal has a lot of potential, but it’s crucial to have a strategy in place for managing the short-term financing risks.

What aspect of real estate are you digging into?