If you can acquire a good property, good neighborhood, good condition at a good price AND you won't lose money month to month... 

If the worse case scenario makes money at all or doesn't lose much, that's GREAT because even if everything goes wrong, things don't go to the dogs.

On a 20-30 year timeline, I don't think there is any losing in this game if you underwrite conservatively.Best of luck to you, and hopefully you can get your feet wet this year!

Not sure what to say about any potential theft, but easiest way is to have it shipped to the cleaners house or you go and personally restock once a month.The potential theft is likely not significant on a yearly basis and if the cleaners are doing a good job and you are making money then I wouldn't lose sleep over it.

At this point we were close to losing the deal since we were running out of time.

That is a lose lose situation. 

You're losing more income than you're saving doing it yourself.

This is not good because who’s to say the business does good for the first couple of months then I lose my housing help I am receiving.

But there are hundreds and thousands of investors buying properties from wholesalers every year and it's pretty unlikely they are all losing money on themI'd also recommend getting multiple contractor bids.

We were going to take out a personal loan from our local credit union to cover the rehab costs, but family has approached us about losing us the funds.