Cash flow on traditional buy-and-hold properties can be tight unless you’re able to secure a deeply discounted deal and keep renovation costs low.That said, I regularly come across off-market properties at strong discounts and have connections with reliable contractors if you need support on that front.

If something goes wrong, it could damage the property or injure someone—and you’ll be the one getting the call (and possibly the bill).Maintenance – Tenants rarely clean or care for them properly.

Some investors prefer to stay unlicensed so they can move more freely and just build strong agent relationships instead.If you’re already active or planning to go all in on flips and buy/sell regularly, it could be worth it.

Maintain regular communication — Stay in touch with all parties, including the title company.

(Which is going to be 2-5x higher than regular insurance which is not the servicers fault its what insurance companies charge and servicers do not own insurance companies). 

While not as sleek or modern in its UI, it offers powerful accounting features, solid messaging automation, and integrations with major software platforms.Ultimately, if your priorities are strong guest communication paired with clean financial tracking, and you're planning to scale or manage properties for others, Guesty or Hostaway are likely your best options.

As someone who supports landlords with bookkeeping and clean reporting, I see a lot of folks burn out trying to solve everything up front when really, like you said, the key is being resourceful and willing to figure things out as you go.Appreciate the insight!

Prioritize Preventative Maintenance: Regularly inspect properties and handle issues early.

Quote from @Ian Tan: How many real estate investors (SFR primarily) regularly check their property taxes and appeal them?

That small monthly spread to the seller ($2500 vs $2300 mortgage) keeps it simple and clean.