$\DeclareMathOperator\Fr{Fr}\DeclareMathOperator\Aut{Aut}\DeclareMathOperator\Diff{Diff}\DeclareMathOperator\Sym{Sym}$Another, more geometric, approach to this question is as follows: let $G$ be a Lie group acting on $M$, and let $P$ be a principal $H$-bundle over $M$. (This addresses your question (2), but it includes (1) if you take $P = \Fr(V)$ to be the frame bundle of the vector bundle $V$.)
Now, if the action of $g \in G$ is supposed to lift to $P$, the least we need is an isomorphism $\psi_g \colon P \to \Phi_g^*P$ of $H$-bundles over $M$. For these to actually provide an action, they must satisfy that $\Phi_g^*\psi_h \circ \psi_g$ agrees with $\psi_{hg}$ under the canonical isomorphism $\Phi_g^*\Phi_h^*P \cong (\Phi_h \circ \Phi_g)^*P \cong \Phi_{hg}^*P$.
This can be rephrased more globally as follows: let $\Aut(P)$ denote the group consisting of all diffeomorphisms $P \to P$ over $M$ (i.e. mapping fibres to fibres) that preserve the $H$-action. That is, these are bundle maps which cover any diffeomorphism $M \to M$. This comes with a projection $p \colon \Aut(P) \to \Diff(M)$. The map $p$ is a group homomorphism, and if we consider only diffeomorphisms isotopic to the identity on $M$, then it is even surjective (you can see this by a cohomology argument, or by endowing $P$ with a connection).
Let $\mathcal{G}(P)$ be the fibre of $p$ over $1_M$ (this is the group of gauge transformations of $P$). We thus have a short exact sequence
$$\mathcal{G}(P) \to \Aut(P) \to \Diff_0(M)\,,$$
where $\Diff_0(M)$ denotes the connected component of $1_M$ in $\Diff(M)$.
This is even a short exact sequence of smooth groups (for instance in the world of diffeological spaces).
Our $G$-action is a smooth group homomorphism $\Phi \colon G \to \Diff(M)$, and I will assume that it factors through $\Diff_0(M)$. (Alternatively, assume that for every $g \in G$ a $\psi_g$ as above exists; otherwise there is no chance of finding a lift of the $G$-action $\Phi$ to $P$ anyway.)
Then, we obtain a pullback sequence
$$\mathcal{G}(P) \to \Sym(P) \to G\,,$$
where $\Sym(P) = \Phi^*\Aut(P)$.
A lifting of the $G$ action on $M$ to one on $P$ is now the same as a splitting of the above short exact sequence of smooth groups. The obstructions to the existence of lifts thus are the obstructions to splitting this sequence smoothly (I am not sure how well non-abelian group cohomology for diffeological groups is developed, but I would expect it to describe the obstructions; if $G$ is discrete, ordinary group cohomology should suffice). If you find lifts, then the sequence shows that these lifts are a torsor over $\mathcal{G}(P)$; this controls how many lifts there are in case there are any. You can also find a bit more about this in Bunk, Müller, and Szabo - Smooth 2-Group Extensions and Symmetries of Bundle Gerbes.