If he’s being banned or just bored.

There are certainly ways around the eviction moratorium put in place by the CDC, and Florida no longer has any statewide eviction bans in place. 

I'd pause on anything with a HOA, lot of hate directed at STR right now in KC....so I would expect HOAs to take a tougher stance and either add in a ban or enforcement of existing bans.

Many markets are putting a lot of restrictions in place around STR's and some have moved to outright ban them. 

Regulations are only increasing, and this can also be outright bans on new rentals entirely. 

The average property is $650k and properties under $400k would be at least a $150k reno.Option 2 sucks - condos have many rental restrictions with HOA's and if they don't now, they could in the future (especially big buildings) many condos restrict or ban STR so that would be a challenge.If I were you, I would spend the next year reading BP, set up Redfin alerts and follow the market, and save more for a down payment. 

The supply of LTR's would increase considerably, or there would be more homes listed for sale, within an area if STR's were banned out right. 

Yup, read the rules. quickest way to get banned on BP

Condos as rentals have potential issues including lack of control as the condo HOA can ban rentals, can dictate flooring, can raise HOA Fees, can enhact a supplemental fee for large capital expense items.

@Alicia Kuluris This may take a while to be beneficial for you, but I believe STR investors in Las Vegas are suing Clark County, NV for banning all STR's.