The current rent is low for the market so there is a potential to increase with total of $300 plus the garage is not rented at the moment which is an extra $150 .I will appreciate any opinion or thoughts!

made digital signatures legal valid signatures.However, a digital signature cannot be notarized - the nature of a notary is a person to person verification and ID check making sure the person signing the doc is who they say they are and they are putting pen to paper in front of the notary.Some documents cannot be digitally signed - Sometimes this is law, sometimes it is policy of whoever / whatever administers the document or the intent of the document.Examples:a purchase contract can be digitally signedFHA will allow buyers to digitally sign some disclosures, but sellers have to wet sign.You can't digitally sign a deed - because it has to be notarized.

. $290-$390 a month for a pro membership and I can hardly use the site or app...Naturally, I downgraded the membership.

If your goal/strategy is to build a nice nest egg for retirement and not replace your current income (not knowing where you are in life), then netting 5% while padding your future isn't that bad of a deal, especially since there are ways you might be able to increase that 5% through property and operational improvements.

Sounds like you could increase your cashflow by 50%.

Some risks I saw come to reality: increasing condo fee, board threatening to pass rental restrictions on units, including on existing landlords/owners.

I also include utilities in the rent so adding a second person increases the utility usage and costs me another $30 or more a month.

If its in a good neighborhood it might increase its value on a long term basis. 

Alone with increasing the number of rentals I also have got in better neighborhoods so better rents.

Take that seriously to increase your chance of success.