I am fairly new to RE investing as well and currently looking at properties in La Crosse which is my hometown, close to St Mary's.

I've taken my fair share of sub2's which is actually more creative so if it works for someone, more power to them.This is very different, though.

If I did purchase this property and take on the current tenants I would not want to maintain the $375/month rate.

Do you have a clause in your lease that the tenant must maintain reasonable heat in the winter?

Just be careful about fair housing laws, as this strategy gets tricky if you ever deny renters to try and hold out for a buyer.

If there isn't anything about a deed restriction, like not being able to resell for 30, 60, or 90 (or sometimes more) days then you can probably double close without any issues.If there is a restriction then you can still usually sell it just for some capped amount (I think usually 20%) more than you paid.If you can carry it then you can also wait out the restriction as well.This should be fairly explicit in the documents and if not then there shouldn't be any issues double closing.

Without a track record, they tend to want a big down payment and have fairly aggressive terms.I suspect, as with any business or finance relationship, if you have a proven track record, you can structure better deals.As far as approaching private lenders, I would start by Googling.

I struggle with talking to people, and having finess while maintaining confidence.

Here is my first thought, remember I am fairly new at this and am not 100% if this would work or even if this deal would be possible to find.I was thinking, find a seller that would be willing to do seller financing and line up a private investor for a 20 - 35% down payment.

The reason I ask is it occurs to me that a possible strategy to get over the hump could be to pay yourself (ie: the entity) rent at fair market value.